Clay CEO Amin Explains Path from $1 Million to $100 Million ARR
Colossus | Investing & Business Podcasts
Capitalism fundamentally rewards high-risk commitments over effort or talent, enabling startups to scale rapidly by treating sales as a flexible creative discipline rather than a rigid set of software tools.
## Background
Published by Colossus | Investing & Business Podcasts on RSS / web on June 16, 2026, this episode of 'Invest Like the Best' features host Patrick O'Shaughnessy interviewing Kareem Amin, co-founder and CEO of Clay. The page description introduces Clay as a fast-growing GTM software company valued at over $4 billion, while highlighting that the discussion covers Kareem's unique leadership philosophies, company-building principles, and personal insights on risk, ambition, and silent meditation retreats.
## TL;DR
Kareem Amin traces Clay's journey from an abstract tool designed to lower the latency between human thought and computation to a $4B+ go-to-market platform that leverages LLMs as a force multiplier. He breaks down how Clay targets creative GTM power users, uses usage-based pricing, and rejects conventional startup playbooks like 'hire fast, fire fast' in favor of repositioning talent and unconventional cultural practices like clowning and magic. Beyond business tactics, Amin explores how operating from a place of personal wholeness rather than internal 'lack' allows leaders to take bold risks, grounding his philosophy in the core values of Courage, Truth, and Justice. He reflects on insights gained from a 10-day silent meditation retreat, musical design analogies like 'building a guitar, not a microwave,' radical communication clarity, and the provocative concept of a 'death doula' for companies that have fulfilled their original mission.
## Atmosphere & style
The conversation feels exceptionally intimate, intellectually rigorous, and philosophical, moving far beyond a standard Silicon Valley founder interview. Kareem Amin speaks with quiet introspection, vulnerability, and poetic precision, while the host acts as an engaged, thoughtful sounding board. The mood shifts seamlessly between deep business strategy, spiritual reflections on silent retreats, and artistic metaphors involving music, magic, and clowning, creating a calm yet profoundly stimulating narrative arc.
## Key takeaways
- `00:00` Clay set out to demystify computation by creating an open-ended, flexible translation layer that puts GTM programming power directly into the hands of non-engineers.
- `05:00` Clay achieved rapid growth from $1M to $100M ARR by treating sales as a creative discipline, serving power users, charging based on usage, and leveraging LLMs as a force multiplier.
- `10:00` Capitalism primarily rewards genuine risk-taking over mere hard work or talent, requiring leaders to pick a vector and commit fully despite the vulnerability to public failure.
- `15:00` Sustained long-term success requires operating with integrity and fairness, as winning through shortcuts or building solely for external adulation leads to empty victories.
- `18:28` Operating from a state of internal wholeness rather than 'lack' enables leaders to take cleaner, bolder risks focused on serving customers rather than seeking validation or preserving ego.
- `21:42` While early startup stages require a 90% focus on direct execution, operating at large scale turns corporate leadership into a public responsibility that demands deep reflection.
- `25:00` Insights from a 10-day silent retreat revealed that obsessing over the future functions as a form of Freud's 'death drive,' whereas present awareness transforms stillness into productive focus.
- `30:00` Clay rejects standard tech playbooks like 'hire fast, fire fast' and underinvested functional roles, instead repositioning struggling employees and empowering creative functions like product managers.
- `34:41` The internal ethos of 're-enchanting the world' draws on the psychology of magic to maintain mystery, wonder, and deep empathy in software and customer interactions.
- `36:27` Music offers fundamental models for business by highlighting the importance of time, silence, and intentional endings when navigating company transitions and offboardings.
- `38:38` Designing software as a 'guitar' rather than a 'microwave' provides users with expressive primitives that offer infinite mastery and creative depth rather than rigid automation.
- `41:20` Founders should optimize for organic discovery and take immediate next steps rather than fabricating artificial long-term visions when one does not exist.
- `44:29` Achieving multi-billion-dollar valuation highlights that material wealth cannot resolve internal feelings of incompleteness or serve as a permanent finish line.
- `45:00` Most organizational friction stems from unstated assumptions, requiring radical clarity and establishing a 'shared reality' when managing teams and employee departures.
- `50:00` The venture ecosystem blindly incentivizes perpetual scaling, whereas companies could benefit from a 'death doula' concept that gracefully sunsets organizations once their core mission is complete.
## Detailed walkthrough
### `00:00` Clay's Origins and the Power of Computation
The conversation opens with a discussion of the long, non-linear journey behind Clay—now valued at over $4 billion—and the core mission that sparked its creation long before the rise of Large Language Models. Co-founders Kareem Amin and Nikola set out with an abstract yet ambitious goal: demystifying computation and putting the power of programming into the hands of non-engineers. Amin reflects on the dynamic nature of the 21st century, where computation has replaced raw materials like oil or steel as the fundamental resource for value creation. Drawing inspiration from music production tools like Ableton Live—where an artist can seamlessly extract an idea from mind to machine—and historic milestones like the 1960s "Mother of All Demos," Amin emphasizes that lowering the latency between having an idea and seeing it manifest on a screen creates a powerful feedback loop for human thought.
Originally, the pair contemplated building tools for software engineers to reinvent the terminal. However, realizing that engineers already hold this leverage, they pivoted toward business users—specifically targeting sales and marketing teams. These departments are brimming with creative go-to-market strategies but historically lacked the technical execution capabilities to realize them at scale. Amin cites a modern example of a client using Google Satellite View to identify commercial properties with accumulated waste to target trash-removal services; Clay acts as the translation layer that makes such complex, non-obvious logic executable without needing custom code.
- **Founders:** Kareem Amin and Nikola (both studied engineering before working in product).
- **Core Inspiration:** Music creation software (Ableton Live), historical computing milestones (1968's "Mother of All Demos"), and reducing latency between thought and execution.
- **Target Audience:** Sales, marketing, and RevOps teams (Go-To-Market engineering).
`05:00` Building for Go-To-Market Alpha and Chapter Two
Amin explains how Clay's distinct philosophy set it apart from typical sales software, which often treats revenue teams as simple "coin-operated" operators. Most competitors try to offer rigid, out-of-the-box tools that deliver pre-packaged answers. In contrast, Clay recognized that sales is inherently a creative discipline requiring "go-to-market alpha"—the ability to experiment, iterate, and stand out from the noise. This counterintuitive approach meant building an open-ended, highly flexible toolkit rather than a simple plug-and-play solution.
When ChatGPT and LLMs emerged, Clay was uniquely positioned to capitalized on the shift. Having already committed by 2022 to serving outbound sales agencies, integrating disparate data providers, and cultivating an open community, the underlying architecture was ready. Because Clay was designed around go-to-market primitives and open API integrations, LLMs acted as a massive force multiplier rather than a disruptive threat. Amin outlines the three foundational assumptions that enabled Clay to grow from $1 million to $100 million in ARR over two years:
1. Treat sales and GTM work as an open-ended creative discipline ("Go-To-Market Engineering").
2. Target RevOps professionals and power users willing to master a powerful, flexible tool.
3. Charge based on usage rather than per-seat licensing to align incentives with team productivity and automation.
> "You need to set everything up so that you're pointing in the right direction so that when the wave comes, you go with it and you're not fighting it."
`10:00` Statues of the Mind: Courage, Truth, and Justice
Reflecting on what actually governs a high-growth company beyond operational tactics, Amin references a vivid vision he had of ancient republics placing public statues in cities to honor foundational civic values like gentleness, courage, or integrity. If he were to place three statues in the central lobby of Clay, they would represent **Courage**, **Truth**, and **Justice**.
Amin breaks down his perspective on **Courage**, challenging the common belief that capitalism purely rewards hard work or raw talent. Pointing out that many people work endlessly or possess extraordinary skills (like sword-swallowing or juggling) without achieving high economic rewards, he argues that capitalism primarily rewards real risk-taking. However, true risk requires stepping into genuine uncertainty with a high potential for personal or public failure. Real risk isn't spreading bets thinly across multiple markets; it requires picking a single vector and committing fully, despite the potential for shame if it fails.
Turning to **Justice**, Amin recounts a surreal encounter outside a movie theater screening of *Stop Making Sense*, where a stranger asked him "What is this?" while borrowing a lighter. For Amin, exploring the vast, mysterious complexity of the world requires societal and organizational stability. Justice provides that baseline stability. Whether managing an economy or leading a tech startup, leaders cannot simply use power or coercion to dominate others without creating friction. Treating employees and customers with fundamental fairness—whether hiring, firing, or resolving disagreements—is the only stable, long-term way to build an institution.
- **Capitalism & Risk:** Capitalism fundamentally rewards calculated risk over mere effort or raw talent.
- **Defining Real Risk:** Experiencing genuine uncertainty paired with a vulnerability to public failure or shame.
- **The Core Statues:** **Courage** (to commit to bold choices), **Truth** (to see reality clearly), and **Justice** (to maintain fairness and long-term organizational stability).
`15:00` Ambition, Integrity, and the Illusion of Adulation
Kareem Amin explores the concept of being "long-term greedy," arguing that the only way to sustain long-term success is by maintaining absolute integrity and ensuring fairness across all interactions. Winning by cheating or cutting short-term corners yields an empty victory that lacks genuine satisfaction. Reflecting on early milestones like raising Clay's Series A and referencing Brian Chesky’s realization upon reaching a $100 billion valuation, Amin emphasizes that building a business solely for external adulation, prestige, or money is a hollow pursuit. For ambitious individuals, internal standards are far stricter than any external metric, because one is always fully aware of their own hidden thoughts, motives, and compromises.
- **Long-term Greed**: True long-term success relies on staying in integrity so that everyone involved experiences fairness along the way.
- **Internal Standards**: External praise is fleeting; an ambitious creator must judge themselves by their own rigorous standards rather than public adulation.
---
`18:28` Optimizing for Self-Respect and Moving Beyond Lack
The conversation turns to a personal practice: waiting an hour after an interaction to write down the singular, lasting insight that remains. In this instance, that key takeaway is optimizing for self-respect above all else as a behavioral North Star. Amin explains how cultivating self-respect and deeply understanding one's true motivations allows leaders to embrace genuine courage and risk. Many founders build out of a sense of internal "lack"—hoping success will earn them love, approval, or validation. Amin shares how a friend's unconditional support helped him realize he could feel complete right now, transitioning him into a state of being "post-lack."
Instead of killing ambition, operating from a place of wholeness allows a founder to take cleaner, bolder risks that serve the customer rather than internal corporate politics or ego preservation. Amin notes that legendary visionaries like Steve Jobs and Jony Ive designed from this generative, whole mindset rather than fear.
> "The more whole you can be, I think the more risks you can take and the more courage you will have because you have nothing to lose."
---
`21:42` Introspection, Execution, and the Burden of Scale
While introspection is essential for transitioning from lack to wholeness, Amin highlights the importance of balancing internal reflection with actual execution. Within a company, a healthy balance looks like 90% execution ("doing") and 10% meta-analysis. Employees often fall into subtle procrastination by obsessing over long-term strategic roadmaps instead of simply taking the immediate next step.
However, as a company or leader grows in scale and public impact, deep reflection becomes an ethical obligation. Using the example of expanding Walmart, Amin notes that building at scale ceases to be a purely private endeavor. Leaders become representatives of the collective environment and must seriously examine the downstream consequences of their power and resource accumulation.
- **Action vs. Analysis**: Maintain a ratio of roughly 90% execution to 10% meta-analysis to avoid operational paralysis.
- **The Responsibility of Scale**: As a company expands, leaders must move past simple resource accumulation and consider the broader societal impact of their success.
---
`25:00` Insights from Silence: The Death Drive and Delicious Boredom
Amin shares a pivotal experience from a 10-day silent meditation retreat focused on a non-dual tradition called Hridaya. Unlike standard breath-focused meditation, this "direct path" involves meditating on the space between breaths or contemplating the perplexing question, *"Who am I?"*
On the seventh day of the retreat, Amin caught himself constantly daydreaming about returning home to explain his insights to friends. This sparked a sudden realization linked to Freud's concept of the "death drive": constantly projecting into or obsessing over the future is essentially an attempt to accelerate toward death, which is the ultimate future outcome. Recognizing this pulled him immediately back into the present moment, transforming what felt like mundane stillness into a state of "delicious boredom." The retreat also exposed his deeply ingrained tendencies toward resource accumulation—whether anxiety over where his next meal was coming from or obsessing over where Clay's next ARR (Annual Recurring Revenue) would originate.
> "Whenever you're picturing the future or anticipating the future, it's kind of like Freud's death drive. The only thing that happens in the future is you die... Thinking about the future is the death drive."
---
`27:27` The Day Five Insight and Capital-T Truth
On the fifth day of his silent retreat, Amin experienced a profound shift in perspective—a felt sense of interconnectedness with all things. Rather than treating empathy as a distant concept of imagining oneself in another's shoes, the experience revealed a deeper reality: other people's suffering and experiences are fundamentally shared.
Connecting this realization back to the core company value of "Truth" (capital-T Truth), Amin describes it as understanding the ultimate nature of reality and human potential. While keeping this perspective top-of-mind during daily startup management remains a constant challenge, he argues it is essential for transcending trivial workplace squabbles and focusing human effort on meaningful, world-changing endeavor.
`30:00` Unconventional Company Building and Taking Bets on People
Running a company unconventionally requires careful storytelling so employees understand the context behind unusual choices rather than feeling like arbitrary beliefs are being forced onto them. Clay intentionally overinvests in areas that typical software companies underinvest in, such as brand, content, community, and unconventional recruiting. A prime example is early employee Mishti, who took on a content role—typically a lower-paid or secondary function in standard startups—and was compensated and treated like a product manager. When taking creative or organizational risks, courage must be paired with long-term commitment rather than abandoning experiments at the first sign of friction.
This long-term commitment directly shapes Clay's approach to talent, standing in stark contrast to the standard Silicon Valley mantra of "hire fast and fire fast." When employees are floundering nine months into their tenure, the leadership team examines whether the role, context, or executive decision-making is holding them back rather than immediately writing them off. In roughly half of these cases, readjusting the environment allows the employee to become a breakout "superstar." Clay's co-founder, Varun Anand, shares the perspective that a lack of fit isn't a moral or skill failure, but simply a misalignment of timing and immediate organizational needs. To foster creative expression, Kareem also introduced the team to the concept of clowning—discovered at a party in San Francisco—viewing it as "edgy improv" that spans physical performance, emotional range, the jester speaking truth to power, and the trickster communicating deeper truths through humor.
- Mishti joined early in a content role but was compensated and empowered at the level of a product manager.
- Clay rejects the rigid "hire fast, fire fast" philosophy, working with struggling employees for over nine months to reposition them into roles where they can succeed.
- The four distinct types of clowning integrated into their cultural repertoire include physical clowning, emotional range, the jester (truth to power), and the trickster (spiritual truths via jokes).
`34:41` Magic, Curiosity, and Re-Enchanting the World
Clay's fascination with the trickster mindset naturally led to a deep appreciation for close-up magicians. Kareem recounts frequenting 69 Atlantic, a hidden 23-seat speakeasy magic venue tucked behind a bookstore, where world-class performers demonstrate that magic is far more than simple "sleight of hand." The best magicians weave narrative storytelling grounded in a sophisticated understanding of human psychology, using their craft to reignite a profound sense of wonder and curiosity.
This perspective directly inspires an internal initiative at Clay termed "re-enchanting the world." In an era increasingly dominated by artificial intelligence, Kareem emphasizes that technology is fundamentally magical, yet people quickly grow desensitized to it. Cultivating a sense of wonder prevents people from assuming they already understand everything about a person or a problem, promoting greater empathy, curiosity, and warmth in everyday customer interactions.
- 69 Atlantic operates as an intimate 23-seat speakeasy magic space in the back of a bookstore hosting top-tier magicians.
- Clay's "re-enchanting the world" ethos aims to preserve a sense of mystery and wonder around software and human interactions.
`36:27` Music, Time, and the Art of Endings
Drawing on his background as a dilettante musician who recently started a band, Kareem explores the fundamental lessons music offers for business leaders. Unlike visual art like paintings, which can be perceived all at once, music requires time and silence to exist. The spaces between notes are as essential as the sounds themselves—a Zen-like realization that "where the room isn't is where we are." Modern executives often focus endlessly on adding features or building new structures without considering what needs to be removed or how an experience unfolds over time.
Music also provides a framework for thinking about narrative structure and endings, an often-neglected aspect of company building. Managing a growing company means overseeing a microcosm of humanity where difficult offboardings and terminations are inevitable. Music offers diverse models for concluding relationships cleanly—whether through a gradual fade in volume, a sudden halt, a quiet whimper, or a build-up of intense energy—helping leaders navigate difficult transitions with intention.
- Music relies fundamentally on two overlooked dimensions in business: time and silence (the spaces between things).
- Executives frequently default to adding elements rather than removing them or managing how narrative experiences unfold over time.
- Musical endings (fade-outs, sudden stops, quiet whimpers, high intensity) serve as a conceptual model for managing employee departures and organizational transitions.
`38:38` The Emancipation of Dissonance and Building Guitars, Not Microwaves
In analyzing music history through an essay titled "The Emancipation of Dissonance," Kareem highlights how Western music evolved by progressively accepting more "dissonant" sounds as harmonious—starting with single octaves, adding perfect fifths in Baroque music, integrating major and minor thirds, incorporating seventh chords in jazz, and eventually embracing microtones and electronic soundscapes. Applied as a product design principle, this concept encourages leaders to examine behaviors or ideas that initially feel "off" or uncomfortable and find the right context where they become useful and harmonious.
This leads to a core distinction in how Clay views software design and go-to-market execution: "we're not building a microwave... we're building a guitar." While a microwave is a functional commodity where every unit performs the same simple task, a guitar consists of just six strings and twelve frets, yet offers a lifetime of depth, mastery, and creative expression. In sales and go-to-market strategies, the goal should not be manufacturing artificial desire, but attaining the idealized form of helpfulness—akin to offering an umbrella the exact moment it begins to rain.
- "The Emancipation of Dissonance" illustrates the historical progression of accepted musical complexity, from octaves and perfect fifths to jazz sevenths, microtones, and ambient sounds.
- Microwaves represent transactional, commoditized software tools, whereas guitars represent expressive platforms requiring skill and offering infinite mastery.
- Idealized go-to-market strategy focuses on timing and meeting genuine customer needs seamlessly rather than fabricating consumer demand.
`41:20` The Role of Vision and Optimizing for Discovery
When addressing whether startup leaders must possess a rigid long-term vision, Kareem grounds the answer in the core value of truth: if a leader has a genuine vision, they should state it clearly, but if they do not, they should never fabricate one. Many historic breakthroughs, from major medical discoveries to detecting the cosmic microwave background radiation, occurred purely through coincidence rather than targeted planning. Forcing a rewritten, neat narrative after the fact obscures the messy, organic reality of innovation for future builders.
Instead of obsessing over a predefined destination, founders are often better served by optimizing for discovery and taking the immediate next logical step. Drawing inspiration from Native American vision quests—where individuals fast in nature to receive guidance—leaders should feel comfortable admitting when they are between visions, allowing space for new directions to emerge naturally. Within Clay's current chapter, however, Kareem maintains a crisp vision: helping every company in the world identify their ideal customer, accelerate outreach, and scale efficiently.
- Key historical breakthroughs, such as the discovery of cosmic microwave background radiation, were accidental rather than planned milestones.
- Kareem advocates optimizing for discovery over fixed destinations, encouraging founders to admit when they lack a clear long-term vision.
- Clay's primary overarching mission is enabling businesses globally to discover and convert their best customers.
`44:29` Wealth, Wholeness, and the Infinite Game
Addressing the topic of personal wealth following Clay's multi-billion-dollar valuation, Kareem reflects candidly on what financial success actually delivers. The core insight gained from achieving extraordinary wealth is that material resources cannot cure internal feelings of inadequacy or incompleteness. Wealth accumulation operates as a continuous, competitive loop rather than a definitive finish line.
- Financial success highlights that wealth cannot resolve internal feelings of incompleteness or lack of self-worth.
- The pursuit of financial status remains an infinite, highly competitive game that requires internal grounding to navigate healthily.
`45:00` Extreme Clarity, Shared Reality, and Communication
Kareem Amin explores the psychological dynamics of raising capital and achieving financial independence, noting a fundamental paradox: to secure a $100 million round, a founder must mentally step into a state of mind where they feel they neither need it nor lack it. Reflecting on his own personality, Amin acknowledges a core "wounding" centered around intense self-reliance—a driving force that makes someone a strong entrepreneur, but one he has actively dialed back to embrace interconnectedness and support from others. Material abundance ultimate restores time back to a founder. Building Clay is now a deliberate choice rather than an existential need for validation or money, empowering him to make bold decisions and take bigger swings without fear.
When discussing organizational friction, Amin reframes the idea that "all problems are communication problems." Issues often stem from unstated assumptions and complex mental game theory rather than actual strategic impasses. His direct approach involves radical clarity: stating his own assumptions, assessing what the other party wants, laying out rational options, and confronting misalignments head-on. When letting someone go at Clay, he seeks to ground the departure in a "shared reality." If a gap in performance or vision cannot be bridged, Amin explicitly takes personal accountability as CEO—stating clearly that he has lost faith in the alignment, rather than shifting blame entirely onto the employee.
* **Handling Offboarding and References:** When parting ways with team members, Amin addresses common fears directly by clarifying how he will talk about them to future employers. He openly admits to prospective callers where the company failed to support the individual or where his own management skills fell short.
* **Contrarian Company Building:** Instead of blindly copying standard playbooks (e.g., how to scale from 150 to 300 employees), Amin deliberately bypasses conventional tech-startup advice. By ignoring typical advice, Clay avoided the standard scaling pitfalls that founders are routinely warned about.
---
`50:00` The Concept of a "Death Doula" for Companies and Knowing When to End
Amin and the host dive into an unorthodox topic rarely discussed in Silicon Valley: the obsession with perpetual scaling and the need for a "death doula" for corporations. Amin criticizes the shallow debate surrounding venture capital versus bootstrapping, arguing that society blindly incentivizes every single business to scale—often ruining the intrinsic quality that made the organization special in the first place (akin to a great local restaurant degrading as it expands). Drawing inspiration from his silent meditation retreat and the historical origins of corporations in the 1500s (such as the East India Company), he questions why companies don't simply disband once their core mission is achieved.
Using Microsoft’s original mission—"a computer on every desk"—as a hypothetical example, Amin questions why institutions pivot into abstract secondary missions rather than celebrating completion. A "death doula for companies" would usher businesses toward graceful endings, allowing them to spin out smaller projects or gracefully sunset rather than becoming bloated "zombie" organizations. He notes that while his daily mental bandwidth is consumed with scaling Clay, he remains hyper-vigilant about ensuring the company builds true value rather than chasing scale for its own sake.
* **Societal Scaling Traps:** Society lacks structural support or grieving processes for dying companies, forcing founders into a perpetual growth loop even when an entity has run its natural course.
* **The Power of Unconditional Support:** When asked about the kindest thing anyone has ever done for him, Amin recalls close friends who told him prior to Clay’s success, *"You don't need to do anything. We just love you anyway."* This unlinking of love from personal achievement allowed him to build Clay from a place of genuine desire rather than seeking validation, cultivating a healthy detachment from the outcome.
## Notable quotes
> `05:00` You need to set everything up so that you're pointing in the right direction so that when the wave comes, you go with it and you're not fighting it. — Kareem Amin
> `18:28` The more whole you can be, I think the more risks you can take and the more courage you will have because you have nothing to lose. — Kareem Amin
> `25:00` Whenever you're picturing the future or anticipating the future, it's kind of like Freud's death drive. The only thing that happens in the future is you die... Thinking about the future is the death drive. — Kareem Amin
> `36:27` Where the room isn't is where we are. — Kareem Amin
> `38:38` We're not building a microwave... we're building a guitar. — Kareem Amin
> `50:00` You don't need to do anything. We just love you anyway. — Friend of Kareem Amin
## Mentioned
Kareem Amin, Nikola, Varun Anand, Mishti, Steve Jobs, Jony Ive, Brian Chesky, Sigmund Freud, Clay, Colossus, Ramp, Vanta, WorkOS, Rogo, Ridgeline, The Podcast Consultant, Ableton Live, ChatGPT, Google Satellite View, Walmart, Microsoft, East India Company, OpenAI, Anthropic, Cursor, Vercel, Mother of All Demos, Stop Making Sense, Hridaya, 69 Atlantic, The Emancipation of Dissonance
Kareem Amin argues that enduring software companies are built by treating software as an expressive craft rather than a commoditized shortcut, while decoupling founder ambition from personal validation. Operating from internal wholeness, radical clarity, and deliberate organizational boundaries enables leaders to take genuine risks and navigate corporate growth with intention.
Building Expressive Tools for Go-to-Market Alpha (5:00)
Clay co-founders Kareem Amin and Nikola set out to bring computational leverage to non-engineers, targeting sales, marketing, and RevOps teams. Rather than treating sales professionals as mechanical operators needing pre-packaged solutions, Clay framed go-to-market work as an open-ended creative discipline requiring "go-to-market alpha." Amin contrasts software designed like a "microwave"—a commoditized appliance producing identical results—with tools built like a "guitar," which impose few rigid constraints while offering infinite depth, skill, and creative mastery.
This thesis enabled Clay to grow from $1 million to $100 million in ARR over two years. Because the company built around open API primitives, served outbound sales agencies, and used usage-based pricing, large language models acted as a force multiplier rather than a disruption. Amin contends that idealized go-to-market execution avoids manufacturing artificial demand, instead timing outreach like offering an umbrella the exact moment it begins to rain.
Internal Wholeness, Real Risk, and Foundational Virtues (10:00)
Amin challenges the notion that capitalism purely rewards effort or raw talent, arguing that economic returns flow primarily to real risk-taking—defined as stepping into genuine uncertainty with exposure to public failure and shame. Clay's operational philosophy rests on three civic values: Courage to commit fully to a single vector, Truth to perceive reality clearly without retrofitted narratives, and Justice to maintain long-term stability and fairness across all employee and customer relationships.
Personally, Amin advocates moving past building from "lack"—the desire to earn validation or love through success. Achieving multi-billion-dollar valuation milestones demonstrated that wealth cannot cure internal inadequacy. Instead, operating from wholeness empowers founders to take cleaner, bolder risks for customers rather than self-preservation. Amin recommends a practical ratio of 90% execution to 10% meta-analysis to prevent strategic paralysis, noting that large-scale operators bear an ethical responsibility to examine the downstream societal effects of their power.
Unconventional Talent Models and Radical Communication (30:00)
Clay rejects Silicon Valley's standard "hire fast, fire fast" philosophy. When employees flounder nine months into their tenure, leadership examines whether role design, organizational context, or executive management created the friction. In roughly half of these cases, readjusting the environment enables the individual to become a high-performing contributor. Clay also overinvests in traditionally undervalued areas, such as compensating early content hires like product managers, while introducing concepts from clowning to broaden creative and emotional range.
When departures prove unavoidable, Amin seeks a "shared reality" through direct communication. Rather than letting unstated assumptions fester, he directly clarifies options, takes personal executive accountability when alignment fails, and transparently details what he will tell future employers—including admitting Clay's own management shortcomings. Drawing on his experience as a musician, Amin views structural transitions and clean endings as an essential discipline in organizational design.
Resisting Perpetual Scaling and Corporate Mortality (50:00)
Amin criticizes the universal incentive for companies to scale indefinitely, arguing that unchecked expansion often destroys the intrinsic quality that made a business special. Drawing on reflections from a 10-day silent meditation retreat—where he linked continuous future projection to Freud's "death drive"—Amin cautions against relentless resource accumulation. He questions why corporations, established conceptually in the 1500s, rarely sunset after achieving their original purpose, citing Microsoft's initial "computer on every desk" mission as an example of a goal that pivoted into secondary objectives rather than reaching completion.
To counter this trap, Amin proposes the concept of a corporate "death doula" to help organizations gracefully dissolve, downsize, or spin out projects once their mission finishes. While focused on scaling Clay's platform to help global companies discover customers, he stresses that founders must know when an effort has run its natural course rather than pursuing scale for its own sake.
Amin leaves unresolved how venture-backed enterprises can practically implement structured endings or withstand relentless capital pressures to perpetually scale without compromising their market position.
[5:00] Kareem Amin: You need to set everything up so that you're pointing in the right direction so that when the wave comes, you go with it and you're not fighting it.
[18:28] Kareem Amin: The more whole you can be, I think the more risks you can take and the more courage you will have because you have nothing to lose.
[25:00] Kareem Amin: Whenever you're picturing the future or anticipating the future, it's kind of like Freud's death drive. The only thing that happens in the future is you die... Thinking about the future is the death drive.
[36:27] Kareem Amin: Where the room isn't is where we are.
[38:38] Kareem Amin: We're not building a microwave... we're building a guitar.
[50:00] Friend of Kareem Amin: You don't need to do anything. We just love you anyway.
Original transcript
[0:00] Ramp is the only platform built to make your finance team leaner, faster, and better, saving businesses 5% annually on average so you can stay focused on growth. Ramp customers grew revenue 3.2 times faster than the average American business. Visa, Vercel, Cursor, Stripe, Notion, 11Lab, Shopify, and 70,000 other businesses all run on Ramp. Mine does too, and so should yours. Learn more at ramp.com slash invest. Felix by Rogo is a personal finance agent that turns a single prompt into finished client-ready work using your firm's own templates, context, and standards. Send Felix an email like, take these comments and turn them for me, or update my tracker with the context of these emails, or run the ability to pay math on this buyer, and Felix sends back finished PowerPoint decks, Excel models, and sourced research. Felix works the way your team already does, delivering work quickly and accurately around the clock. Learn more at rogo.ai slash Felix. The best AI and software companies from OpenAI to Cursor to Perplexity use WorkOS to become enterprise ready overnight, not in months. Visit WorkOS.com to skip the unglamorous infrastructure work and focus on your product. Hello and welcome everyone I Patrick O and this is Invest Like the Best This show is an open exploration of markets ideas stories and strategies that will help you better invest both your time and your money If you enjoy these conversations and want to go deeper, check out Colossus, our quarterly publication with in-depth profiles of the people shaping business and investing. You can find Colossus along with all of our podcasts at colossus.com. Patrick O'Shaughnessy is the CEO of Positive Sum, All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit PSUM.VC. My guest today is Kareem Amin, co-founder and CEO of Clay. Clay has become one of the fastest growing software companies of the last few years, valued at over $4 billion. It helps companies find their customers and reach them at scale. But this conversation is about a lot more than Clay. Kareem is one of the most original founders and thinkers that I've met recently. We talk about the statues he keeps at the center of how he runs Clay truth justice and courage and what those words demand of him in practice We talk about risk ambition and what he learned about both I had a lot of conversations with Kareem over the years and this is one that I remember Please enjoy this great conversation with Kareem Amin. Can you describe the long, strange journey you've been on, why you started, and then what it was like to exist and have done some interesting stuff when this thing happened and then how you took advantage of it? I find the two-chapter story so interesting. We started with the really abstract ambition of how do we give the power of programming to more people. My co-founder, Nikola, and I, we worked in product even though we both studied engineering. I think it was really just, hey, you're in the 21st century. You have computers that can do things for you. And if you can't tell them what to do, then you can't capture any of the value that's being created. We had a lot of ideas and we wanted to build them. And every time we tried to build something, it was taking so long. I was also starting to play around with producing music. And I really like tools like Ableton Live. I have an idea. I can extract it from my mind and into the machine. And we were also in this kick of like looking at the history of computation, things like in the 1960s, the mother of all demos, just seeing the fluidity of the interaction between you and a computer needs to be super fluid for it actually to lead you to the next stage of thinking You need low latency between I have an idea it happened And because we were coding we felt that adrenaline that everybody feeling right now which is hey I can tell the machine to do something and it does In the 21st century, the material is computation. If in the past it was oil or steel or whatever it is, today it's computation. So the more we can give that to more people, the more interesting things happen, the more egalitarian it is. It's kind of interesting because that was our desire and there were no LLMs, which we started off by thinking about the terminal and we're like, how do we reinvent the terminal where engineers are spending all of their time? And then we're like, well, that's just going to speed up engineers. We need to find something that gives that power to more people. In 2017, we started thinking, do we give it to engineers or non-engineers? Do we give it to consumers or business users? We ended up deciding business users for a variety of reasons. Within that, we're like, okay, which department in a business actually has a ton of ideas but isn't able to execute them? And landed on sales and marketing where we think people are really creative, but they don't have the ability to turn a lot of their ideas into reality. I'll give you one example that's real today that is kind of wild,
[5:00] I have one company that sells to businesses that have a lot of garbage. So now they're using Google, what's called Satellite View, to see which areas have a lot of accumulation of garbage. And then they figure out, OK, that's a good business to sell to. That's an idea that you might have, but it might be super hard to execute that at scale. And now something like Clay can actually translate that for you. Because of that, because the whole intention around Clay was how do we give the power of programming to people, That's kind of how the name came, because we're like, OK, it's go to market. But now you're an engineer. We came up with that before it was really possible to use LLMs to fully code. But it was how do you systematically think about a problem and break it down and then execute it? We've also kept that ethos in the company. That's what makes us really different than everybody else in our space. There are simple things that we've been saying out loud, but I think people don't really believe that that's why it works. So one is it's a creative task. So if it's a creative task, we need to leave it somewhat open ended. A lot of companies that counter position to Clay or in the space are like, hey, what you really want is salespeople are people have literally used the word coin operated So what you need is something that super easy to use It gives you the answer It tells you who you selling to and what you saying And it just works Whereas we think you always need in sales to find go-to-market alpha. How are you different than everybody else? Otherwise, it's just noise. In order to do that, you need to have a really powerful tool that allows you to experiment quickly and try things out and see what works. So we built that instead, which was very counterintuitive. Describe the takeoff of chapter two of now LLM's come out. What that moment felt like, what the subchapters have been. Yeah. What's interesting in that story that is maybe worth talking a bit more about is that this was back in 2022. We had made a decision to say, OK, we are targeting go to market teams, specifically sales. Specifically, we're going to start with outbound. Specifically, we're going to start with people who want to get data from lots of different data providers in order to do outbound. In fact, it's going to be agencies and not startups. And we're going to do a lot of what we're doing and support them in public and build a community. So we took a lot of decisions that I think were non-obvious. The main thing that happened was really the courage and commitment I think to making those decisions that actually allowed the company to take off because the company was already taking off before ChatGPT came out We were well set up to include LLMs in Clay because one, we were set up to allow any integration to anything. And two, we were a coding like product just designed with go to market primitives. As soon as we had LLMs, it just boosted everything. So for Clay, there were three core assumptions that we made. And I actually think this is how to build a really big company and one that grows really quickly. So we went from one to 100 in two years, but that wouldn't work if we weren't pointing in the right direction. So you need to kind of set everything up so that you're pointing in the right direction so that when the wave comes, you go with it and you're not fighting it. For us, we made a couple of decisions. One, Dupline and GoToMarket are creative, and so we're going to give them the most powerful tool. If you were going to give the most powerful tool instead of the simple out-of-the-box tool, then you need to find the right customer or user for it. For that, we said, okay, we're doing it for RevOps, which is an existing kind of role, and we going to call the subset or the word jobs to be done GoToMarket engineering to give it a framing This is the tasks to be done are all the things that you need to do the activities to grow your business, remove any obstacles to growth. The last part was we're going to charge for usage instead of proceed because we're trying to get more productivity. So if you have fewer people, we didn't want that to be something that is an anti-incentive for us. If you just look at those three decisions. Almost every other decision in the company falls immediately out of those. Anyone can come up with what we should do next if you believe these three things. That's the best way also to run a company that's growing really quickly because I have to just communicate to you these are the three things that we're assuming. And whenever you're making a decision, check to see if it works within these three concepts. I feel like people don't talk enough about the things that actually matter in building a business. I had this dream actually where it was kind of like a vision where I saw lots of statues in a modern city, but I was wondering like, oh, we don't build statues anymore. But I'm like, if you look at old republics, they would have statues for concepts like courage or integrity or gentleness.
[10:00] And there are like gods for these different things. And I feel like we've forgotten these abstract kind of ideas that matter in the moment when you're building a company. It was actually, hey, you need courage to make a leap and commit to these ideas and then see what is the logical conclusion if we take these ideas seriously all the way to the end. If you could put three statues off the elevator in the lobby, what three would you build? courage, truth, and justice are the ones that come to mind. Say like one click more about each. Why those are? I think courage because one thing that I think a lot about is I think capitalism rewards risk more than anything else. I think a lot of people think it's like meritocracy or hard work, which I think is silly. There are a lot of people working really hard and not making a lot of money. So it's not hard work. There's some correlation there, but it's definitely not just that. It doesn't just reward skill. There's a lot of really skilled people. There are people who do things that I can't even dream of. You're eating a sword or you're juggling and they're not making as much money as someone doing a YouTube video It clear again that that not the case I do think it rewards risk which makes sense I don have a strong comment on whether that good or bad I just trying to figure out what's actually happening. There's a lot of people who think they're taking risks, but aren't taking real risks. I talked to one founder who went to a good school, then went to YC, and then was telling me about his company. And he's like, we serve sales and we serve recruiting. And I was like, you have to pick one. This is where you're actually providing value. In picking, committing yourself to serving some group of people in some specific way. For me, at least my definition of risk or how I've experienced it is you need to not know what's going to happen genuinely. You're going to discover something new. I think it needs to be coupled with a high potential for shame. It needs to be you can fail in a way that feels scary or maybe associated with shame. And when you're doing that, you're genuinely about to discover something new and learn from it. And that's when you can take real risks. And to do that, you then need to have many traits. One of them is courage. It's amazing. How about truth and justice? Let take justice for a second I want to live in a stable society that allows me to kind of like have the time and space to think of things I think the world is pretty crazy I went to see this movie called Stop Making Sense I was downstairs in the movie theater I had a joint that I was about to smoke and I was trying to light it up but I didn have a lighter I asked the guy who was standing there I was like hey can I borrow your lighter and he was like sure can I ask you a question I was like yeah of course and he was like what is this and I was like what do you mean this whole thing he was like yeah what is this and I was like well that's a big question I think like the world is a mysterious and amazing place and I feel like there's so much to know we're just starting to make progress on how wonderfully weird it is. And we should be spending more time like exploring that. And to do that, I feel like we need stability. So to get stability, I think you need to have justice between people. I think there's no stable way for some group of people to dominate others. It just doesn't work. No matter how strong you think you the other person is a tremendous nuisance if they feel like they treated unfairly So there no stable configuration around that And if you thinking about the economy or like countries you can't bluster your way out of it. You can't say we're the strongest. Even when I'm saying that, I have to remember when I have power over people, you tend to be like, they must do what I want because I want them to because I control this. It's just not a stable configuration. You can get by for a little bit And then you get tremendous pushback. So I think that having the value of justice, one thing I think about is like, how do you treat people with respect and fairness all the time in every situation, whether you're hiring them or firing them or you're disagreeing over what they should be doing? So I think that that maybe is what's fueling this democratization. Even people are stable in a place where they feel like they have the opportunity to get what you've gotten to as long as there's some fair chance for that. And they're okay with what they've gotten if they feel like, hey, this is what's available to me at the moment. This is just kind of like an internal thing that I've had. I used to play soccer even on my team if I feel like we fouled the other team and we could get away with it I would have like a really weird thing of integrity this feels off. Do you have a sense of where that came from?
[15:00] nature nurture? It feels like it's some intuitive knowing for myself that I'm a long-term greedy person. One of the things we talk a lot about to the company is like, how do you be long-term greedy? And I think the only way to be long-term greedy is to stay in integrity for people to feel like there's justice all the way along. I think it's also just like a belief in yourself. You don't have to cheat in the short term to get something. You're going to win. Let's say you're playing a soccer game, you feel like you cheated or like this wasn't fair and then you won. It doesn't feel as good. I did hear your interview with Brian Chesky's, the statement he made around getting to $100 billion and feeling like shit. Yeah, I actually felt like I related and we're obviously in a much smaller spot. But even early on, when we raised our series A, I remember having that sensation of if you're doing this to get adulation or to get prestige or to make some money, there's no end to that. It's kind of like an empty thing that passes. The only judge of anything is yourself and your own self You have to be doing it so that you feel like what you done is interesting and worthwhile When you an ambitious person your judgment is actually way higher than anyone else because you know everything that you're thinking and you know everything that you've done. So I know everything that I'm thinking about or doing and my standards are higher than anyone else. Vanta automates security and compliance for over 16,000 fast moving companies like Ramp, Cursor, and Harvey, keeping them audit ready around the clock. It's the number one agentic trust platform, and it now helps companies like yours watch for the risks that show up between audits across your vendors, your AI tools, and your whole environment. 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Ridgeline is the first end system of record with embedded AI for investment management firms running portfolio accounting reconciliation reporting trading and compliance on one unified platform Firms are moving off legacy technology and onto Ridgeline because of how far ahead Ridgeline's AI features are compared to anything else in investment management software, which is why I believe that firms that come out ahead in the AI era will be the ones running on Ridgeline's unified platform. If you're serious about your firm's AI strategy, Ridgeline should be part of that conversation. You can request a demo at ridgeline.ai. There's this thing I like to do where when I spend some time with somebody, I wait an hour and then I write down notes in my phone. I like benefit from the hour. It's like a cleansing function or something like whatever lasts in my brain through that hour. Like I want to write down when we last were together. This is the one thing I wrote down, which was this notion of optimizing for self-respect over everything else as like the North Star for behaving. I'm curious how that relates back to risk and courage. Do you think those things are related? Do you think it's possible to help people become more courageous and take more risk? For sure. I think in order to do that, you just need to understand your mind and your motivations more and be more honest about them So again back to the saying simple things honestly it very hard to admit to yourself I think why you doing something Even if you look at the narratives for companies, none of them have any relation to the motivation of the founders, and we don't talk about that in public. For me, for example, it's like, why am I building a company? do I think that I will be more liked or loved if I do something that is a success at a world-class level? Can I get that now? I've had friends come up to me that are like, hey, I don't care if you succeed or fail. I love you. And I was like, wow, that's actually helpful. I didn't think it would be, but it's feeding some part of my desire must be fueled by that. But I can get that right now. And now I can start to take real risks where I'm thinking about the business and not trying to fill this particular need. VCs have this common trope that is, hey, we invest in someone that has a chip on their shoulder or has some kind of lack that they're trying to fulfill. And this is common across creative work. The trope is like you're depressed or you're anxious or whatever, and you're trying to fill that, and you're actually afraid to lose that depression or anxiety or whatever it is because you feel like you'll be less...
[20:00] productive or creative. Through my journey, I had this moment where I was like, you know what, I'm not going to create from a place of lack anymore. And I went around probably pretty annoyingly telling people, I have everything I need. I'm good. Post-lack. Post-lack, yeah. It's a great negotiation leverage because there's nothing you can give me. I feel great. I'm already complete. From there, you can still create. I think people are misunderstanding, tremendously misunderstanding this, in my opinion. If we were in a post-scarcity world, no one will do anything. Everybody will just be hanging out. I was like, have you been to Burning Man? People are still doing stuff and they have things you can create from a place of wholeness. And in fact, you will be less destructive in the world. I think you'll create less damage. We keep thinking here like, hey, let's think of our customers. What are we trying to give them? Why do people keep saying customers first? It's because when you're in a company, things start to happen where it's like this person's thinking about their career or this person wants to please this other person. They're not thinking about the customer. They're just thinking about the internal dynamics. The more whole you can be, I think the more risks you can take and the more courage you will have because you have nothing to lose. It funny to me that perhaps the most interesting duo in modern business history Johnny Ive and Steve Jobs were like almost undoubtedly creating from this generative place I don't know if they've used the same terminology or something, but you read it all like it's all there. They're the most adored, but maybe the least emulated. It demands the question, the things that got you to this sense of wholeness from this place of lack. There's been much strange debate about the role of introspection in business and in general. Naively, I would say like it's introspection that's a key tool in the toolkit to get from one to the other. Curious what your experience has been or what you would offer about that. I kind of understand the motivation here, because one thing I talk a lot about here and have thought for myself is the amount of work that's doing versus meta-analysis can sometimes flip. So you should be like 90% of the time doing and then 10% of the time meta-analyzing. At work, we've had this happen a lot. And I talk to the team a lot about it. where people are like, hey, what is going to happen in one year? Why are we building this feature instead of that feature? And I'm like, is that stopping you from taking the next step in your job? If not, then you're procrastinating. My sense is his conversation around that. I think his example is Walmart If you trying to build more Walmarts yes you should always be thinking about wake up in the morning build more Walmarts But at some scale when Walmart is affecting all of us if you don't think about why you're building Walmart, or what more Walmarts do to us, or to a shared environment, that responsibility is on you. I think that the more you make, and the more successful you become, it is part of your responsibility back to all of us to think about what you're doing, that you're our representative now. You're not a completely independent actor. And in fact, we have the power to pull some of that stuff back from you. So is there anything that you did in particular going from kind of lack to wholeness? For me, I think the introspection is it was a journey to kind of understand like why ambition. So I was suspicious of my own ambition. I was like, what am I trying to get out of this? part of why the company took some time to take off was because I was grappling with that. And that led me to investigate which parts of me are trying to kind of be expressed through this. And that was just my own personal interest. I just found that I couldn't just do something without understanding my motivation for it because I was looking at people who are further ahead in my field If you a great business person or you built a great company I was like do I want that I think it also coming from like valuing my time and myself I was having this experience where I like what if I took myself really seriously? You could take yourself lightly and just be like, well, these are just thoughts. I want to do something big, so do other people. Or take it really seriously and be like, why do I want to do that? What would I actually offer the world if I was able to do that? And then thinking like, hey, you can succeed and create a lot of damage in the world. I think a lot about death. When you're deathbed, like, what are you thinking? How does it feel in that moment? If you had a moment to reflect, how do you judge yourself? And there's like the experience of every day and living a life that you feel is worthwhile on a day to day basis. And there's also like, how did you impact the world if you did impact it? And I wanted to make sure that I felt like I really grappled with that correctly. And I didn't just try to accumulate resources and just be like, hey, I did something big. I accumulated some resources. It does go back to this like justice principle. It's like if you're going to do something big, you need to kind of think about the consequences of you taking that role because it's just a role. It's a really cool thought exercise to say, OK, play out the thing I'm doing to its natural extreme. Do I want that state? No one does that. I had one time where I
[25:00] I remember when I was much younger, I was like, oh, like I want to make a lot of money and then I'll be a philanthropist. And I'm like, is that actually useful? There are a lot of philanthropists. Is it working? Are they actually impacting the world? Could we move faster in some other kind of formula or like setup? Or is it just that I want the control to pick the causes that I want? Maybe one more thing on the death thing that I think is kind of interesting was like my own insight that I had. I went on this 10 day silent retreat a while back. I thought I was going to just go think it was not that. It was kind of like a spiritual experience. It was called Herodaya, not like a Vipassana. Their approach, there's like a non-dual approach to meditation, where typically you kind of like meditate on your breath or some object, whereas in non-dual traditions, it's called the direct path. And in the direct path, you meditate on the space between the breaths, or you ask the question, who am I? A very frustrating question. I would say I would not recommend it. but anyway i'm doing this thing on the fifth day i have like this big insight where i'm like i figured it out i got it then on the seventh day i'm like okay well what now i start imagining going back and telling my friends about this insight but i like i not here i just imagining the future i kept wanting to go towards the end And then I had this big flash of insight that I try to remember But it said whenever you're picturing the future or anticipating the future, it's kind of like Freud's death drive. The only thing that happens in the future is you die, the far future, whatever it is. And so you're accelerating that. And as soon as I had that thought, it's kind of the death drive. Thinking about the future is the death drive. And so I like immediately felt back in my own body in the moment and felt the boredom of where I was. And I was like, wow, this is such delicious boredom. I finally got that insight, which is I'm so grateful to be bored right now because it's so amazing. I also realized that I have this scarcity, like food scarcity. I was thinking constantly about food and where am I going to eat? And then I just had this one P and it exploded in my head. I was like, this is too much. I can't. But I realized that I haven't accumulation tendency where I'm like, where's the food going to come from? And in the company, I noticed I'm like, where's the next ARR going to come from? Now I'm aware of that. And I'm like aware of when I have enough and then I can take more risk. I don't need to accumulate something that way beyond actually what we need What was the day five insight or was that the insight itself It hard to describe because it an experiential thing i think it was a momentary experience of like this understanding what matters or something like that because i felt like oh i'm connected to all things really bizarrely just feeling like hey i am a component or like a part of this whole thing and i'm connected to all things and they all matter. I had kind of this thought of one, I'm no better and no worse than anyone else. But also, it made me feel like this real empathy when I see someone who's suffering. I'm just like, oh, they're also me. Not I empathize with them as if I was them. I'm like, this is actually me. That's kind of like a really out there thought or a belief. Strange thing is it's actually not at all. Like it's like the longest lasting set of beliefs in the deepest, richest philosophical traditions. Yeah. Today it's still... This is an abstract idea today, but quite an old one. It used to be kind of like a common thing, supported with religion. But to me, what was crazy wasn't the idea. It was the experience of really feeling that. And then knowing that when I hear something in Buddhism that just freedom of all beings or knowing that the suffering of one person is the suffering of everyone So back to the justice thing Well I can solve everybody problems And in fact, that would be hurting me to try to help someone when I don't have capacity. But to really know every single person, they're carrying it for me rather than they fucked up or they screwed up. And I'm better because I worked hard and did X, Y and Z. Just to bring it back to our statutes, is that then truth? The day five insight? Is that just truth? Yeah, if we go back to capital T truth, it's understanding that. And then I understand why in philosophical traditions or even in religions, they're like remembrance. I can get that momentary understanding, but then remembering it in the moment when I'm making a decision about my business or about like my personal life is very tricky. But I do think that that is what's necessary for us to get to the next stage of what's interesting in the world. There's so many mysteries, so many interesting things. And I feel probably like many other people that were squabbling in circular ways around the same nonsense. My real anger is like, what are we doing? We're wasting our human potential, wasting our time. If I hear and digest all of that, and then I imagine, OK, this guy is now running a software startup. I'm,
[30:00] imagine that that startup is run in some unusual ways. So I'm curious what those are and why you arrived at unusual ways of running the business. Yes, there are some unusual ways in which we run the business. But also, I think it's important to be careful of how much you push ideas onto other people or project onto them your beliefs and also to remember what context you're working on. It's almost like telling a story. If this is the normal way to run a business and then you think that it's this completely bizarro way over here, you also need to take the steps to tell the story. And I think it's the same in product development. I can't just give you a product that you have no context for. You don't even understand how to interact with it. It's like, hey, these are my personal beliefs and my interests that are underlying some of the normal activities that we do. and then there's adjustments that we make. I'd say the first and most important way is that it's a felt experience in the company of how we treat people and how we think about their personal development, but there are concrete ways in which it shows up. One way is that we overinvest in things that people typically underinvest in We overinvested in recruiting in brand in content in community building We've hired people who are very overqualified in some of these roles who are doing it for the first time. For example, we published an article about this with one person who was an early employee, Mishti. She took a content role. She would have never taken a content role. It's typically kind of not the most highly paid thing in a company or it's extra. and we compensated her like a PM and we're like, go do it. So we take those kinds of risks and then we stick with it. I think another thing, by the way, with risks is when you couple risks and courage, the next part is commitment. You actually need to kind of follow through to see what actually ends up happening. You can't just quit in the beginning. We take that seriously. And if we see somebody is really skilled or has some star potential, we stay with it for way longer than most. Everybody talks about hiring fast and firing fast. We've had people who nine months in were floundering and we're like, this person is excellent. I know they are. But what's going on here? Is it the role? Is it the context? Is it our decision making that's limiting them? Eventually we find an amazing spot for that person and they become a superstar 50 of the time The other 50 of the time this person might be really special but we just can create the conditions for them or they're too far away. One thing that I've talked to my co-founder, Varunat, is like we're never pissed off when someone doesn't work out. We're like, hey, you're just we're here and you're here maybe along the journey. One day you'll get there, but you're not getting there fast enough. You don't have what we need at this moment. So I don't even have a opinion on whether you're good or bad. people were like this person was good this person was bad were you good in the moment that we needed you to be you might also be super skilled but you just didn't perform here i've had people who are incredible i know they're incredible and they couldn't perform here for a variety of reasons and they've gone to other places and done a really good job so i think it's important to be nuanced there are some other things where i think some of the things that people have covered about us in the past i like clowning for example i discovered clowning what's clowning exactly i think i was an SF at a party and someone was telling me that they were going to go to this clowning workshop and I was like, what is that? I think of it as like edgy improv. There's kind of like four types of clowning. Physical clowning, which is the one you would imagine when you think of clowning. There is emotional range. Let me make you happy, then make you sad, then make you happy so you can feel the full range There the jester which is like telling truth to power Then there the trickster which I think is pretty interesting which is how do I tell you like spiritual truths through jokes You realize, hey, everything does change. That's like a truth about the world, but I get you to experience that. We are really into magicians at Clay. We incorporate it into our events or things that we do, and we take risks. Our brand takes a lot of risks, way more risks than I think general B2B brands. And that's why people love the brand and the company. It's authentic to us, but it's also honest. It's trying to really cut through and be like, hey, we think you'll be interested in this and we're not hedging. I think a lot of times people are authentic but hedging. So they're not really saying what they want to say because they're afraid of the consequences. What have you learned from magicians? I actually think the trickster thing is the thing that's been a common thread between us. There's this place called 69 Atlantic that we had been going to like. It's a small speakeasy magic, close-up magic. There's like 23 spaces in the back of this bookstore. And they get like world-class magicians every month. And the...
[35:00] The thing that I remember from these really incredible magicians is it's not just a slate of hand thing. There's a storytelling component. It's kind of wild. A lot of them are telling a story of like a deep understanding of how your mind works or how the world works, where they're like, hey, I'm showing you this thing. And really what they're trying to do is to spark curiosity. We're going to do something about this at Clay. We're calling it re-enchanting the world. in a world where there is AI, it's literally magic in some form. And to remember that this is magic, a lot of these things that we're sitting in front of are still magic. It's pretty wild. And to re-enchant the world again and not make it like this boring place where you think you understand how it works, because you really don't. So I think they're doing simple things to reignite that feeling of wonder. And I think if you take that feeling of wonder actually in your everyday life. You're a more friendly person because you're not like, oh, I understand how this person works or I understand how this is. You're like more curious. It makes you more curious about our customers and makes us interact in a more pleasant way because we're like, oh, there's stuff to learn here I think what I been actually getting from this magic stuff is been like remembering what it feels like to be like I have no idea how this is working I can even begin to comprehend how to think about it I know that it a trick but I can figure it out For whatever reason this makes me wonder the same question about music the role that music plays and has played in your life and what you've learned from your many, many experiences with music. Well, I'm a dilettante musician, but I actually just started a band. I was talking to another famous musician who was calling me because he's starting a company. And I'm like, wow, I'm going the opposite direction, man. But I was reading this piece that was super interesting for me. And one of the key things I think with music versus other things is time. You can't listen to a song without time. Time is actually a core component and silence is a core component, like the spaces between things. So it's a good reminder that those are like fundamental things that you have to work with. It's like very Zen. Where the room isn't is where we are. If this room was full of things, we couldn't sit in here. And we only think about making things. We don't think about removing things. And we don't think about things unfolding. I think video is also like that. But a painting isn't. You can see it all at once. So I think about narrative. How are you telling the story? How are you bringing people along with you on the journey You can tell everyone everything all at once It overwhelming because you had time to process They haven This piece that I was reading it was talking about endings We always think about beginnings but we don really think about endings when you starting a company or not Well, what about all the people that I'm going to fire? And so many crazy things genuinely happen. As soon as you have a large number of people, you're dealing with a microcosm of humanity. You're running like a mini society. So it was like, hey, we can look to music to think about the different forms of endings and learn from that. Some songs end as just like repeating and it goes down in volume. Some things end suddenly. It's like a whimper or intensity. You can think of these as different ways to end something. Another one that I think is really cool, this was an essay that I read that was called The Emancipation of Dissonance, which first of all is a really cool title but it was theorizing the history of music as a history of accepting more sounds as music so in the beginning it was just maybe drumming first it's like the tonic you play the c and then the c an octave above and then it was adding the fifth that why it called the perfect fifth a lot of baroque music had that and then people started adding the third which is what creates chords minor and major chords And initially that was resisted People are like what the hell is this This feels off But then you add the seventh where you get jazz. And people were like, that's unacceptable. Like this is not music. And then eventually you start to add more and more tones. So this was arguing for in Western music, there's 12 notes, but in Arabic music or Indian, there's 24. And there's other scales that you can use that have even more tones. You can use microtones. Now that you have electronic music, you can make any kind of sound. I think this idea of accepting more sounds as music is actually a helpful product principle, just a way of being where you can start to think, what are all these other ways of being that you think are off that actually could be productive or useful if you put them in the right context. It seems also like an interesting through line is in the world we're going into how important it will be to make people feel something, but maybe also something new. If we can create anything, the logos of it all is, yeah, whatever, you can create anything you want, that the pathos becomes really important on top of that. Insights for music is like make people feel something new. We use this a lot, bring it back, I guess, to the business. I've been telling people
[40:00] Like, hey, we're not building a microwave. Microwaves are useful, but they're commoditized. You just go and say, hey, one minute, heat it. It does what it needs to do. There's no difference between most of them. But we're building a guitar. With a guitar, there's just six strings and 12 frets. But you could spend your whole life just getting better at that. And you can only be playing one style of music. And it's still like new. If you bring that to sales or go to market things, it can feel like a crazy stretch if you actually respect that discipline and be like, hey, what is the ultimate version of sales, marketing or customer success? That's why it's called go to market. In my opinion, it's just like, how do I take the thing that I made and give it to you when you need it? If I really, truly was like, hey, what's the idealized form of this? That's what it is. It's raining. I bring an umbrella. You are like, great, thank you. That's what you actually want to get to. And I think there's a place where I made something, especially as people make so many new things and you happen to need it and it's very niche and I'm able to find you and give it to you without necessarily manufacturing that desire in you Ideally if you need something we can get it for you because we happen to be making it We thinking about all of the creative ways to figure that out One really interesting conversation you and I have had before is about the role of vision in company building and the leader's responsibility or lack thereof to have one in the first place or to have one sometimes. I'd love you to riff on the leader's role and responsibility to have or not have a vision. I think when we were having that discussion, too, my instinct is to go one level deeper or at least that's how it's coming up in me. Let's turn it back to one of our statues, truth. You need to say the truth. So if you don't have a vision, then you don't have a vision. If you do have a vision, then you do have a vision. I think it's important to not say something that actually isn't happening. That's my answer to that, is that I do think ultimately you need to have some guiding principle or some compass, but you don't need that at all times and you don't need to force it. If you just know what the next step is, you should take the next step. And sometimes things happen in all kinds of ways. Most of medical discoveries are complete coincidences. So many of the most advanced things, the cosmic microwave background, complete coincidence. You couldn have gone out and said I want to discover the cosmic microwave background There so many of these things And so I think we telling ourselves a story that is not true about the nature of discovery and how it happens And I think we do a disservice to everybody when we go back and retell the story in a way that is not honest, because it confuses the people who are on the path of figuring it out. So for me, a much more honest version, let's say you're starting a company and you don't know what to do. So many people have that problem. You're like, OK, I want to start a company. I don't even know why I want to start a company, but I feel like this is what I want to do. You don't need to have a reason. And then you can go and start doing things. And once you find something, you can be like, OK, this is interesting to me now. All the stories of greatness are like I was 13 and I saw this one thing and then I dedicated my whole life to it. And I think that happens. And it also happens in other ways. Optimize for discovery rather than destination would be like one way to think about it. Leave the space for the opportunity to discover. If you do have a vision, you should be clear about that and clear how confident you are in that. And if you don't have a vision, I don't think that's a problem. I think you can take the next step and allow the vision to come. In Native American traditions, there are things called vision quests, where you go and fast for a few days and you asking for a vision Sometimes you need to do things in order to get the vision of what you supposed to do And by the way in companies it also could change over time So you might have a vision and then either the vision is wrong or a lot of companies who started five, six years ago that are confused now because things have changed. Well, it's time to change the vision and you don't need to settle on a new one immediately. You can say, hey, we don't know what we're doing right now and we can take the immediate next step in what we're doing right now and wait to receive that vision. Do you feel like you have a vision right now? Yeah. Right now, I feel pretty clear. And within the scope of what we're doing, what the vision is, we're helping every company in the world find who their best customer is and find more of them and accelerate that. What about the notion of wealth? You've also in these two chapters had this interesting experience of now because of Clay's success, you've achieved a level of wealth that by any measure is extraordinary. what has that process been like and what has it taught you that's a very taboo topic i know that's why it's interesting my experience is the initial thing that i had thought is true is that if you're not feeling whole in yourself there's no amount of wealth that fills that it doesn't change that because it's a continuous competitive game it's a loop i was telling someone if you want to raise
[45:00] $100 million, you need to first feel like you don't need that. Paradoxically, also that you already have that. In order to raise money, you need to be like, I have $100 million in my bank account. How does that feel? Act accordingly. Because you need to act like you don't need it, and you have the confidence. Maybe my own core wounding is I have this super heightened self-reliance where I feel like I don't need other people, and I can do everything myself, which is partially why I think it's helpful to be an entrepreneur. And what I've been doing is dialing that down to be like, no, I'm interconnected with people. I do need people. In fact, I need help. I need support. I also rely on so many things. But I think what material abundance gives you is the reality also of your time back. And I'm choosing, for example, to build this company. I don't have to. I don't need anything. I don't need it to succeed more. I don't need to make more money or whatever it is. I'm choosing what I want to be doing with my time. And that goes back to that truth part that's really empowering. I can make my own choices and I can test things out in the world and see if they work or not. I not scared or worried about what happens But I also needed to have that point of view in order to get here Having the opportunity to choose what I do with my time and to take bigger swings that feels really important. And then it's like, what responsibility do I owe back to society? You also once said to me that all problems are communication problems. I'm curious how you've gotten better or what you've learned about not falling into that trap. It's not that all problems are communication. problems, it's that we might have a disagreement or different needs, but often we can't resolve it because we're making assumptions about each other. We're doing all kinds of like game theory things about what would happen if you did this, if I did that, rather than being able to like explain clearly. And even within that, I think it's kind of like in negotiations, you might have different strategies, but my strategy is to be as clear as possible about what I want, what I think you want, and then what the possible options, assuming that you are really intelligent, can read and have access to the same information as me. I need to know what you want and what are the options available. And then we might still disagree, but at least we are disagreeing from a place of clarity rather than from a place of misunderstanding That very very difficult to do Let say we asking someone to leave clay which I think is a difficult thing You can do it in a way, I think, that in most cases, as long as the person is in a shared reality with us, in a way that is based on clear communication. Do you think it's working here? I don't for these reasons. What do you think? And maybe you're like, no, it is working. And I was just like, okay, let's bridge the gap because we can get to a place where it's like, I don't want to be giving you negative feedback every single day. That's not fun for me. I can't imagine that it's fun for you. So then why do you want to be here? And here are the gaps between us. At one point, I told someone, hey, listen, I've lost faith in the ability for you to bridge the gap. I'm the CEO, so it's not a good situation for you. It doesn't make sense. And even if you think you can get there, I'm taking responsibility for that. I'm not saying that this is rational, even. It's just, I can't do it. And that's it. In that case, it doesn't really make sense for you to continue working here. And I want to share that with you because I want to be like direct and clear about it and also own up that this is my call. Like any relationship, there's no compulsion. A lot of people actually really appreciate that and are just like okay I get it I wish that it was different but it not So I going to do something else Most times if someone leaving what are they worried about They worried about what are you going to say in the future to other people So I tell them, hey, if someone calls me up, I'm going to say it didn't work in these ways, but I think these are their strengths. Here are the gaps that we have in our organization that didn't support them. How do you not think about that? When I call up a reference, it's like, can you tell me what was wrong with your company at the time? Because it wasn't perfect. It's always about someone else. It's obviously not true. There are times when my management skills weren't there to handle this particular person or the company itself was not working. And so it creates a really bad vibe for everybody inside. When things are working, things are working. When things are hard, only a few people can handle that. The reason I'm saying these things, by the way, is I'm like, these are the things that I think are actually interesting. Part of my experience of building a company was I just wanted to know through building it and being given the hard choices of how to relate to people or given a quick profit versus a long profit, what would I do? And what's the experience that other people who are making these choices are facing? And I think we're not talking about these things because the risk is too high, right? Like if I talk about what I'm doing in a company and how...
[50:00] on treating people, maybe someone will sue you or customers will lose faith in you. I really feel like companies are built through rules of thumb where I'm like, hey, how do you scale from 100 to 300? And then I talk to five people who've done it and they tell me. And by the way, I've done things that are completely the opposite of that. And it's worked. And the reality is back to the risk. When you're going from 150, for example, to 300 people, you don't wanna take the risk of doing something new. You're like, these people did it. But then you're gonna get the same problems that they had. So many people told me there would be all these weird problems scaling 50 to 300 people. None of them happened. We have some other things that happened, but I didn't have the typical problems because I didn't do it the typical way. As we approach the end, I have one more question about endings. I'm realizing I take a lot of notes after our various meetings over the years. The first time we met, the idea that I remember writing down was you told me something like you wish that there was something like a death doula for companies. And then earlier today, we were talking about this idea that scaling isn't just some universal good. So these are related in my mind. And I'd love you to end by just riffing on this death doula and scaling concept. I'm just like, why are we not talking about whether it is good to scale every business People talk about it a little bit in this like really boring super worn out way of should you raise VC capital or should you bootstrap Completely not interesting ways of talking about it. But it's like if you had a donut business, should you try to scale it? What does scaling it entail? What do you lose when you scale it? Should we be as a society incentivizing all businesses to scale? And we all know this problem, which is like, hey, this restaurant was really good. Now it sucks. So because I think there's a life cycle to things and maybe part of this meditation retreat and thinking about the death thing, I've been thinking about like, is there a life cycle to companies and should we just be OK with that? I'll pick Microsoft for a second because I think it's an easy example, but hopefully they don't hate me for this. You have an initial put a computer on every desk. I remember that mission when I was a kid. You did put a computer on every desk. But now the mission is devices and services and do cool things. Once you achieve a mission, the idea of a company, I think, started in the 1500s. I think it was the East India Company or something. So you get together for a purpose and then you do it. And then should you disband or should you keep like the minimal number of people I think the crypto people have had some of these ideas OK you built the layer Now you move on to the next layer I do think it worthwhile as all this disruption is happening to start thinking about the new ways of doing this I curious about it. A death doula for companies is, hey, if your company has achieved its mission, should we help it pass? Maybe it should have children and people come out and they do cool stuff. But maybe we can institutionalize these things rather than trying to scale things that become zombies or become worse versions of their former selves and then complain about it when we're incentivizing everybody to scale no matter what. I wake up every day and I think, how do I make more clay? I literally think about it. It's consuming all of the CPU time in my brain. In my friend group, they're all thinking about this because I just keep talking to them about it. So if that's what's happening, should we set up some kind of structures to be like, well, what happens when you scale everywhere? I don't just care about scaling. I care about how is this creating value in the world? People are talking about those, I don't know, 1,500 unicorns, if some of them are zombies, how can we help them? Dianized stuff. You need some grieving, you need a possibility to move on. We don't have support for that for companies, and I think it's because no one talks about endings. When you and I are together, I feel like we always talk a little bit about Clay and a lot a bit about even more interesting things And Clay is very interesting This has been yet another example of one of those conversations I loved having it When I do these I ask everyone the same traditional final question What is the kindest thing that anyone's ever done for you? The one that's coming to my mind immediately, I had already mentioned, actually, but it's a few friends have come up to me before Clay succeeded and were like, hey, you don't need to do anything. We just love you anyway. And then I realized, I don't care what they're doing. I don't care what they achieve. I just implicitly like this person and love them. And knowing that I had that, and then I could give that back to myself as well, without any achievement, because I think my childhood wounding was feeling like, oh, I must achieve in order to have care and love. And I was like, I actually don't need that. It created a ton of clarity, where I was like, oh, I'm doing things because I want to, not because I need something from it. So I think Clay is just the output of a lot of thoughts and things. And we're doing it in a way, for me, I hope, where I'm not attached. I'm not attached because I don't need anything from it. I want it to evolve the way it wants to evolve. Thank you so much for your time. Yeah, thank you, bud. If you enjoyed this episode, visit Colossus.com. You'll find every episode.
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