Zip Co-Founder Zaparde Shifts Startup Strategy to Enterprise Sales Risk After FlightCar Operations Trap Cash

FlightCar遭遇资金困局后，Zip联合创始人Zaparde将创业策略转向企业销售风险 二次创业者通过摒弃形象管理，以严格的冷触达验证瞄准成熟企业市场并取得成功。 该对话记录了Rujul Zaparde的成长蜕变：从最初在FlightCar应对严苛运营与利润挤压挑战、在意外界眼光的初次创业者，转变为Zip极具战略定力的领导者。在Airbnb加深对企业规模化的理解并在Y Combinator指导初创企业后，Rujul将第一性原理应用于他的第二次创业。通过执行严格的冷触达外呼销售策略并强力推动早期商业化变现，他和联合创始人成功发掘了采购领域的深层市场需求。最终，本次梳理为二次创业者勾勒出一个底层框架：将对内部本质真相的执着探求和运营执行置于外部认可与形象管理之上。 初次创业者往往过度关注外界评价、董事会印象及媒体报道，而二次创业者则转变为只专注于追求事实真相、打造真正切合用户需求产品的自由心态。 (0:00) 在完成3.7亿美元融资后，企业采购软件公司 Zip 的投后估值已达22亿美元，团队规模扩展至约350人。 (0:00) 首个创业项目 FlightCar 源于在 Panera Bread 仅一小时的仓促头脑风暴，其重资产、低毛利的商业模式严重依赖榨干“柠檬的最后一滴汁”，导致后期融资极其艰难。 (1:37) 为验证真正的产品市场契合度，Zip 坚持前10家客户必须通过全冷启动方式签下，并通过大量 LinkedIn 调研构建出至今仍驱动业务的外拓销售能力。 (18:19) 早期定价应避免免费或滥用“设计伙伴”标签，敢于收取1万至2万美元能及早检验客户痛点是否真实且值得付费。 (20:20)

Drawing on lessons from his operationally burdensome first startup and product experience at Airbnb, Zip co-founder Rahul explains how shifting from external impression management to an internal pursuit of truth helped scale the procurement software firm to a $2.2 billion valuation. Operational Friction and Unit Economics at Flight Car (3:58) Rahul's first startup, Flight Car—conceived during a one-hour brainstorm in late 2012 or early 2013 and launched during Y Combinator's Winter 2013 batch—highlighted the hazards of asset-heavy businesses. The company offered free airport parking by renting out travelers' idle vehicles, initially launching out of a BART transit lot and sourcing fleet vehicles via round trips to San Jose. Although Flight Car eventually scaled to 17 airport locations, it was burdened by facility leases, shuttle fleets, and daily vehicle maintenance. Rahul likened the business model to squeezing the final drop of juice out of a lemon: poor gross margins meant that any minor operational error eradicated profitability. This dynamic created an adverse feedback loop, as low margins compressed valuation multiples and hindered fundraising. Flight Car was rejected by 79 out of 80 venture firms during its Series A raise and reached two weeks of remaining runway before securing a lead investor, illustrating how execution-heavy physical logistics can impair venture viability. Corporate Scaling Lessons and Founder Alignment (9:52) After selling Flight Car, Rahul joined Airbnb as a product manager on the experiences team, seeking exposure to high-caliber product, design, and engineering practices. During his two and a half years at the company, the product management organization grew from roughly 30 to more than 100 PMs alongside thousands of engineers. He noted that without careful organizational alignment, scaling can introduce self-inflicted internal friction, as staff may invent unneeded initiatives to justify roles or gain promotions. Observing CEO Brian Chesky's granular involvement in product quality reinforced the value of what was later coined 'founder mode'—challenging whether internal projects deliver core market value. Rahul later applied these observations as a YC visiting partner during the Winter 2020 batch, navigating early COVID-19 disruptions alongside resilient cohorts such as Whatnot and PostHog, which cemented his view that enduring founders require an intense drive to force ideas to work. Targeting Execution Risk and Validating Enterprise Demand (17:10) Rahul left to co-found Zip alongside former Airbnb engineering colleague Lou on March 31, 2020. Entering Y Combinator's Summer 2020 batch without a settled concept, the team executed a mid-batch pivot following advice from YC partner Dalton. Dalton urged them to tackle an established sector characterized by execution risk rather than unproven market demand by identifying legacy software incumbents that had failed to evolve. This led the duo to target corporate procurement workflows. Lacking prior enterprise sales experience, the founders instituted a rule requiring their first 10 customers to be closed entirely through cold outreach, refusing to rely on warm network introductions. They sent daily LinkedIn connection requests to procurement professionals, requesting advice rather than pitching. After gathering a 107-page dossier of industry feedback, they built the software to address those stated pain points and returned to the same contacts for product demonstrations, transforming cold prospects into initial paying customers. Disciplined Early Pricing and the Second-Time Mindset (20:20) To establish definitive market demand, Rahul cautions founders against offering free pilots or hiding behind 'design partner' labels. He advocates charging early amounts, such as $10,000 to $20,000 annually, arguing that for mid-sized firms of 100 to 200 employees, such amounts are routine expenditures. If a prospect refuses to pay, it provides clear signal that the problem being addressed lacks sufficient urgency, signaling the need for product revisions or a pivot. Rahul contrasts this second startup journey with his first company, where he constantly worried about press coverage, employee departures, and maintaining an upbeat facade for board members. Running Zip—which has reached roughly 350 employees, $370 million in funding, and a $2.2 billion valuation following a Series D round—he treats time as the scarce resource. He structures board meetings and internal reviews around analyzing operational vulnerabilities and seeking unfiltered truth rather than managing external impressions. Rahul attributes Zip's enterprise momentum to lessons learned from earlier missteps: selecting an incumbent market with clear budget, forcing early cold monetization, and abandoning external impression management in favor of identifying operational weaknesses.

Zip 联合创始人 Rahul 总结其创办 Flight Car、任职 Airbnb 及创立企业采购软件 Zip 的历程指出，二次创业的核心优势在于摆脱外界舆论包袱，转向以“探寻商业真理”为导向的战略选择。通过规避重资产低毛利赛道、在成熟软件品类中承担执行风险，并以全冷启动与早期付费严苛验证刚需，创始人得以在高确定性领域建立稳固的企业级业务壁垒。 从重资产困境到挑选执行风险赛道 (7:09) Rahul 反思其早期创办的机场租车平台 Flight Car 时指出，重资产且运营密集的商业模式极难盈利。Flight Car 曾扩张至 17 个机场网点，需要维持大量场地租赁、班车接驳以及每日数百辆汽车的清洗与加油，固定成本高昂。Rahul 将其比喻为“挤柠檬”，企业往往只能依靠挤出的最后一滴汁水赚取微薄利润，早期任何运营失误都会彻底吞噬收益。由于毛利率极低，Flight Car 在寻求 A 轮融资时遭到 80 家风投机构中 79 家的拒绝，甚至一度陷入仅剩两周薪资现金流的绝境。 这一挫折促使他在二次创业时彻底转变赛道选择逻辑。在加入 YC 孵化期间，合伙人 Dalton 建议第二期创业者应避开市场风险，转而寻找“执行风险”领域——即寻找长期未曾演进的传统软件品类，结合外部环境变迁构建新解法。这一建议推动团队转向企业采购流程领域，并于 2020 年创立 Zip。与教育全新市场不同，采购审批与 ERP 对接属于高确定性赛道，成败完全取决于产品与交付执行力。目前 Zip 员工约 350 人，累计融资 3.7 亿美元，最新 D 轮估值达到 22 亿美元。 审视规模化陷阱与创始人模式 (9:52) 在结束 Flight Car 后，Rahul 进入 Airbnb 担任产品经理以学习顶级科技公司的团队运作规范。在他任职的两年半内，公司产品经理从约 30 人扩充至 100 人以上，伴随数千名工程师的加入。这一快速扩张期让 Rahul 察觉到大型组织的内部内耗风险：当企业招募了缺乏明确业务支撑的过量人手时，员工往往会自发编造项目以证明岗位必要性或谋求晋升。Rahul 认为，企业必须警惕此类“自我施加的痛苦”，公司的主要痛感应来自外部市场挑战，而非内部利益错配所引发的消耗。 这一观察促使他深刻认同 Airbnb 首席执行官 Brian Chesky 所践行的“创始人模式”（founder mode）。Rahul 强调，创始人必须保持对产品细节的高标准关注，在组织内部建立健康的质疑机制，敢于提出尖锐问题，持续检验各项业务是否真正服务于公司目标，而非沦为员工个人职业晋升的垫脚石。这些反思构成了他日后管理 Zip 时的团队建设准则。 严苛的市场验证：冷启动与早期付费 (18:19) 在开拓 Zip 的早期市场时，团队缺乏企业销售背景，因此确立了一项严苛的验证规则：前 10 家客户必须完全通过冷启动（Cold Outreach）签约，严禁依赖熟人引荐、朋友关系或既有人脉网络。Rahul 坚信，唯有素昧平生的外部决策者愿意付费，才能证明产品具备真正的市场契合度（PMF）。团队通过耗尽每日 LinkedIn 好友申请配额，以“请教行业痛点”的名义开展沟通，在两至三周内梳理出厚达 107 页的反馈纪要，随后针对性开发功能并向访谈对象展示交付成果，借此成功完成首批客户转化并建立了后续延用的主动获客体系。 针对早期定价，Rahul 明确反对免费模式或以“设计合作伙伴”为由规避收费。他指出，创始人因产品尚不完善而不敢要价是常见误区，但只要痛点足够剧烈、解决方案承诺成立，企业客户就应当付费。他建议早期向中型企业直接收取每年 1 万至 2 万美元的标准服务费，这一金额对百人规模企业并不构成实质负担；若客户在此价位上拒绝买单，往往直接说明痛点不够刚需，提示创始人必须立即调整方向或转型。早期收费能够有效过滤无效建议，确保迭代反馈完全来自拥有切身利益诉求的真实客户。 彻底的寻真意识：放下外在虚荣负担 (22:05) 回顾两次创业经历，Rahul 认为心态上最深远的变化在于从“关注外界虚名”转向“纯粹追求真理”。首次辍学创业时，他长期受制于外部评价体系，时刻担忧高管离职对团队军心的打击、试图在董事会上向投资人粉饰业务太平，并高度在意媒体的曝光与评价。这种过度迎合外界眼光的包袱不仅加剧了精神消耗，也极易掩盖真实的运营危机。 在创办 Zip 时，Rahul 意识到创业者最昂贵的资产是自身的时间，唯一有意义的工作就是打造真正被市场需要且切实可行的产品。这种心态转变促使他将董事会从“汇报表演”重新定义为“排查业务故障的工具”，主动把大部分会议时间用于剖析公司现存的漏洞与缺陷。他认为，彻底放弃对正面虚像的执念、专注于直面核心问题，是二次创业者最具有解放意义的心智跃迁。 Rahul 的复盘展现了企业级软件从盲目试错到理性推演的标准路径，突出了从重资产低毛利泥潭转向高软件毛利赛道、依托纯冷启动与前置付费过滤虚假需求，以及以“创始人模式”遏制大公司病的实践价值。然而，这种以“承担执行风险、避开市场风险”的打法高度依赖创始人提炼传统行业隐性痛点与精细运营销售管道的能力，对于缺乏成熟企业运作背景或面对高度定制化采购环境的初创团队而言，如何低成本穿透传统采购生态仍需经受市场检验。

[0:00] Rahul: You know what, it's my time. I just want to build something that people want, that really works. [1:37] Rahul: Free airport parking by renting out your car, fully insured. [3:58] Paul Graham: That sounds like a thing you guys can figure out... you need to launch tomorrow. [7:09] Rahul: Making money in a business is like squeezing the juice out of the lemon... Flight Car was the type of business where it's the last drop out of the lemon that's the money you keep. [9:52] null: It kind of feels like you went to a bus stop and just picked up everybody from the bus stop and that's who works at your company. [17:10] Dalton: guys, what are you doing? [18:19] Rahul: remember that conversation we had? Your feedback was so helpful to us that we in fact we built it, can we show it to you? [22:05] Rahul: what's broken in the business

[0:00] was a first time founder right I I [0:01] dropped out of school like I cared a lot [0:04] about what others thought what my team [0:07] thought the leaders thought right like [0:08] oh well people quit because this person [0:10] the story executive comes in and then [0:11] leaves I cared what our investors really [0:14] thought right like oh like how is the [0:16] board meeting going to go like how do we [0:18] like paint a positive picture about the [0:20] business and press and all this other [0:22] stuff you care about a lot of these [0:24] things and then the second time you [0:26] really are like you know what it's my [0:28] time I just want to build something that [0:30] people want that like really [0:35] [Music] [0:37] works I'm here with my friend rul the [0:40] founder of zip and we're going to talk [0:42] today about what he's learned as a [0:44] two-time Founder as well as employee of [0:46] Airbnb as well as visiting partner at y [0:49] combinator so to get us started what is [0:52] zip what do you guys do what's your [0:54] two-line description uh tell us about it [0:56] yeah so zip is a procurement software [0:58] company uh and so we provide one front [1:00] door for any employee in an organization [1:03] to request a purchase and we route it [1:04] for approval across you know budget and [1:06] legal and it and security and all the [1:09] different teams before connecting into [1:11] the Erp Financial system you guys have [1:13] done really well you were just you're in [1:15] the summer 20 batch and now you're a [1:17] pretty legit company I mean I I don't [1:19] know what the public numbers you can [1:20] disclose are around valuation or money [1:23] raised or revenue or employees whatever [1:25] you can share I'd love to hear yeah so [1:27] the company is about 350 is people uh ra [1:29] raised about $370 million now and the [1:33] most recent round was our series D at [1:34] 2.2 billion post last month I love to [1:37] hear the story of flight car um let's [1:41] set the stage you were very young Y and [1:44] you started a start up so so take it [1:46] away like how did flight car get started [1:48] yeah so this was back in like late 2012 [1:50] early 13 I dropped out of college and uh [1:54] I remember so this was technically still [1:57] in high school really uh so my [1:59] co-founder dropped out a freshman year [2:01] uh I dropped out of just before freshman [2:03] year actually uh so and you know I [2:06] remember I I called up uh Kevin my [2:08] co-founder and was like hey maybe we [2:10] should like let's do a company together [2:12] uh and you know he was like uh okay uh [2:16] like I'm free this weekend uh and like [2:20] let's chat through ideas and he was like [2:21] I've got to go somewhere but let's meet [2:23] up at you know I grew up in New Jersey [2:25] the local hangout spot of course was [2:27] Panera Brett uh right in in Princeton uh [2:30] right near where I grew up and so we [2:32] agreed on a Sunday to meet up at Panera [2:34] Bread for an hour uh before Kevin had to [2:36] go run somewhere and we were like let's [2:38] just think about the best idea uh let's [2:41] try to come up with the best idea we can [2:43] in the hour and then like let's just do [2:45] it and he's like hey you know have you [2:46] heard of this thing uh it's called [2:49] Airbnb uh and I was like no I've never [2:51] heard of that and he's like well people [2:53] are sharing their homes with other [2:54] people and I was like no way like really [2:58] uh and and you know we kind of just [2:59] started started talking we're like well [3:00] if people are you know what's the most [3:02] expensive thing you own your home and if [3:04] people are sharing that well the second [3:06] most expensive thing people own it's [3:08] generally their car when are they not [3:09] using their car when they're traveling [3:11] uh and this is you have to remember like [3:13] pre Uber and lift like really you know I [3:15] mean they must have been early stage [3:17] companies at best and uh and so we were [3:19] like yeah car you know we would we would [3:22] potentially do car sharing but at the [3:24] airport when people are not using their [3:25] cars they're traveling and other people [3:27] are coming in and and you know they can [3:29] rent the car and and so that's how [3:30] flight car was born free Airport parking [3:32] by renting out your car fully insured [3:34] that was the oneliner that one hour led [3:37] to five years of doing that company uh [3:40] and uh and so the second time around I [3:42] took a very different approach but uh [3:45] but I would really encourage that like [3:47] you you know if you're thinking about [3:48] doing a company like you really put the [3:51] right level of thought into the idea [3:53] more than an hour at least yeah at least [3:55] more than an hour yeah yeah um and so [3:58] you have all these funny anecdotes um [3:59] you guys did such a great job of doing [4:01] things that don't scale can you just [4:03] share some of the anecdotes for how you [4:04] got your first customers and how you got [4:05] it off the ground we actually had a [4:07] bunch of crazy stories so I remember we [4:08] we were in the winter 2013 YC batch and [4:12] we hadn't launched uh uh yet uh and so [4:15] this is like I remember doing office [4:17] hours distinctly with PG like two weeks [4:19] into the batch uh and PG is like oh so [4:22] like how many customers do you have and [4:23] I remember we were like well we haven't [4:25] launched so we have no customers and he [4:27] was like well why don't you why haven't [4:29] you launched and we're like well we [4:30] don't have a parking lot to park [4:32] people's cars and I was like well that [4:34] doesn't like that sounds like a thing [4:35] you guys can figure out uh like you need [4:37] to launch like tomorrow uh and we really [4:40] took it to heart we're like we need to [4:41] launch um and and looking back like that [4:43] was the right advice you know for for us [4:45] because that's how you get feedback and [4:48] so we were like okay well where would we [4:50] park the cars uh and we were like well [4:52] there's a Bart which is the the local [4:54] Bay Area uh like transit system there's [4:56] like a huge like basically Subway [4:58] parking lot at bar which is like 5 [5:00] minutes from the SFO airport we can just [5:03] park there and so we literally launched [5:05] like within a couple of days and we we [5:07] basically would meet our customer at [5:09] Bart get in the car drop them off at the [5:12] airport and then come back and then we [5:14] told them we would park the car but we [5:15] would just park it at Barton and I [5:17] remember it was two bucks a day so it [5:18] was pretty cheap and what happened was [5:20] that then turned into like 200 cars [5:24] parked at Bart uh over the course of [5:26] like 3 weeks and it got like we had [5:28] increased so much parking there that it [5:30] got reported to the BART police which [5:32] they have their own police force it so [5:33] turns out uh and we basically like the [5:36] cops called us they were like you need [5:37] to get these cars out and we had nowhere [5:39] to put these hundreds of cars so we then [5:41] switched to an undercover operation [5:43] where we would not wear flight car [5:45] uniform or anything else and meet people [5:47] like you know get their cars and park it [5:50] uh and then eventually you know we we [5:51] got another parking lot but like that [5:54] was like an example of like just uh you [5:56] know we had to be so Scrappy I mean [5:57] there's so many other uh uh I mean I [6:00] remember early on we were like you know [6:02] in a marketplace right you need Supply [6:03] and you need demand and so you have to [6:04] solve for the supply you have to fake it [6:06] initially and uh and so we uh one [6:09] compounding challenge was that we were [6:11] three co-founders one of whom uh not me [6:13] but one of whom did not have a license [6:15] we couldn't drive and none of you guys [6:16] were old enough to rent a car were you [6:18] and yeah we were all I think 18 and so [6:20] you know like a lot of car rental [6:21] agencies do not rent to like 18-year-old [6:23] kids for good reason uh and so we found [6:26] this uh company called like super cheap [6:28] car rental and San Jose or something and [6:31] this dude was like yeah I'll rent you [6:33] guys like 30 40 you know crappy base [6:36] model Corollas uh and so we were like [6:38] great uh and so we actually just me and [6:40] my one of my co-founders we literally [6:42] took the Cal Train down to San Jose and [6:44] drove up a car one at a time like 15 [6:47] times each which is terrible and then [6:49] parked it at the same Bart lot and [6:51] that's what we initially started Supply [6:54] that's how we got Supply uh and so you [6:56] know you you realize like doing such an [6:58] operationally intensive business [6:59] business like like flight car when you [7:01] have to like do something Scrappy it's [7:03] like at a it's like almost at a comical [7:05] extreme you know compared to like [7:07] running a B2B SAS company today you [7:09] spent an hour thinking about the idea [7:11] you spent five years working on it and [7:13] as I recall you got some real scale you [7:15] guys raised a fair amount of money like [7:16] what's the what was like the summary or [7:18] the postm morem on what happened with [7:19] fight car at our Peak we had 17 [7:21] different airport locations it was a [7:23] very um we didn't take like we took a [7:25] very uh sort of asset heavy sort of [7:28] approach right we had like leases for at [7:30] 17 different airport facilities we had [7:32] shuttle services to and from the airport [7:34] I mean we were washing and gassing up [7:38] like hundreds of cars every day like it [7:40] was a very very operationally intensive [7:42] business and uh and and I I sort of [7:45] equated to like if you think about like [7:46] making money in a business um is like [7:49] kind of like you know if you have a [7:50] lemon it's like squeezing the juice out [7:51] of the lemon and like what's left is [7:54] like the money you make flight car was [7:55] the type of business where you know it's [7:57] the last drop out of the lemon that's [7:59] the money you keep and so if you screw [8:01] up squeezing the lemon earlier you don't [8:02] need to squeeze the rest of it to [8:05] understand that you are not making any [8:06] money right and it was a very very very [8:09] sort of poor gross margin business [8:11] because you have all this fixed [8:12] expenditure and so one very key thing is [8:17] start a business that is a higher margin [8:20] business uh right and that's why the [8:22] idea matters it's almost like instead of [8:23] going to college you went to like the [8:25] hardest boot camp I can ever imagine [8:27] which is here's a really lowet [8:30] asset heavy [8:32] business good luck at the airport and [8:35] you spent Five Years on that that was [8:36] your early 20s you learned so much about [8:39] um what to not do I [8:42] feel you know in an experience like that [8:44] the problem with margins by the way [8:45] because like oh well why are low margins [8:47] bad well if it weren't obvious like it's [8:49] they're bad because of a couple of [8:51] things one it means you're multiple as a [8:53] company is lower you're less likely to [8:56] be able to raise money because you have [8:57] a lower margin business so it's harder [8:59] you have a lower multiple yet and this [9:00] is key you need the money more [9:02] desperately because you have a low [9:04] margin business and so you have this [9:05] really negative feedback loop and and I [9:08] mean flight car I mean we almost ran out [9:10] of money so many times I mean I I even [9:12] remember our series a I pitched I got to [9:15] know a lot of people because I pitched [9:16] like 80 different firms uh nearly all of [9:19] whom except for one said no and I [9:21] remember at a point where we had like [9:23] two weeks of cash left and we were like [9:26] uh you know payroll Cycles are every two [9:28] weeks so we had just done executed the [9:30] cycle and we're like we can't even make [9:32] the next one you know when do you tell [9:34] the team that you don't have enough [9:35] money to run the payroll right like that [9:37] was I remember distinctly having that [9:39] conversation and we got lucky uh and we [9:42] we had somebody lead the a but we went [9:43] through a lot of moments like that um [9:46] and uh and so one key thing was just [9:48] yeah you want to set yourself up with a [9:50] positive feedback loop not a negative so [9:52] you ended up I think selling the company [9:54] and I think you ended up joining Airbnb [9:56] as an employee can you just kind of set [9:57] up the the context thing and then I'd [10:00] love to hear what it was like working at [10:01] Airbnb uh during that time period so [10:04] what happened um was you know I knew [10:07] after flight car um that I wanted to do [10:09] another company I knew I was going to do [10:11] another startup but I felt like in [10:13] reflecting I had never worked anywhere [10:14] like I'd never worked at a real company [10:16] and so what you miss when you don't work [10:18] at a real company is like I think a lot [10:20] of the basic stuff like how do companies [10:22] like even generally work at scale and [10:24] like what is like the best in class like [10:27] what do great engineers and designers [10:29] and you know like what do those people [10:31] look like like how do they work right [10:33] and and actually I remember one of the [10:35] reasons I reflected and realized I need [10:37] to needed to learn this was uh we had [10:39] hired a a marketing leader at flight car [10:41] and I remember like she starts and then [10:44] one week into the job she in my [10:46] oneon-one with her she's like you know R [10:48] like it kind of feels like you went to a [10:51] bus stop and just picked up everybody [10:53] from the bus stop and like that's who [10:54] works at your [10:55] company it's like wow like that's that's [10:59] tough [11:00] feedback but like looking back like you [11:03] know there was there was some truth to [11:04] that if I'm being honest and and so I [11:06] was like you know what this is not [11:07] acceptable like I need to you know I [11:09] need to learn this and so um of course [11:11] you know a company that I always had a [11:13] tremendous amount of uh sort of affinity [11:15] for was was Airbnb and yeah makes sense [11:17] uh and so you know ended up joining uh [11:19] uh as as a product manager uh at at [11:21] Airbnb and and certainly learned not [11:25] just a lot about like what you know how [11:27] like um sort of best-in-class product [11:29] are built so I worked early on on the [11:31] experiences team which is where I met my [11:32] co-founder Lou um and we actually a lot [11:35] of our early team actually comes from [11:36] that experiences team at at Airbnb um [11:39] but it was great to see Brian chesky [11:40] that the CEO be so involved in all the [11:43] details of the experiences product and I [11:45] mean just at a such a critical level of [11:47] quality that like I I definitely learned [11:50] a lot from from sort of seeing that uh [11:52] and so that was one of the things that [11:53] I'd set up for but I also I think [11:55] learned at airb at the time the company [11:58] had grown a lot um I think I was the if [12:00] I remember I was like the 30th or [12:01] something product manager um and then [12:04] when I left almost 3 years later two and [12:06] a half years later there were like a [12:08] hundred something product managers uh so [12:10] I mean and that's just product managers [12:12] you know and then you look at Engineers [12:13] I mean it's thousands and thousands of [12:15] people uh hundreds and hundreds of [12:16] designers and and you sort of realize [12:19] like it's so important to have the right [12:21] incentives for your team members because [12:23] you don't want to create situations [12:25] where you have a lot of people that uh [12:28] were hired because maybe some people [12:30] wanted to you know build up their [12:32] functions or teams and there wasn't [12:34] maybe the best justification for them [12:36] and then of course you Can't Blame A [12:37] Certain you know designer for wanting to [12:39] build something because they were [12:40] literally hired and so they have to [12:42] produce something you don't want as a [12:44] company to have that much self-inflicted [12:46] pain like you already get enough pain [12:48] from external sources right like how do [12:50] you make sure that like most of the pain [12:52] you're experiencing as a company is [12:53] externally inflicted not self-inflicted [12:55] you were at the retreat we had um where [12:59] the founder mode it was not called that [13:01] at the time it was just branchesi [13:02] talking and PG turned uh he coined the [13:05] phrase founder mode but you were there [13:06] and again you worked at airb me in the [13:09] Years where they were growing so fast do [13:11] you have any thoughts on the whole thing [13:13] it absolutely resonated with me uh and I [13:16] also at the same time I love Airbnb like [13:18] I could not be more happy uh that uh you [13:22] know that like there's so much change uh [13:25] that was executed and delivered within [13:27] within the you know within the company U [13:28] but certainly I can totally see how um [13:32] you know there was there was like there [13:33] was a need for change right uh and like [13:36] a need for like creating conflict within [13:38] the company to actually ask the hard [13:39] questions and say hey do we need these [13:41] folks or are or you know are we are we [13:44] actually doing this project because [13:45] somebody actually needs to execute this [13:47] project so that they can get promoted [13:49] versus like the com this is the right [13:50] thing for the company you've had a a [13:53] unique experience as a Founder where [13:54] you've actually worked at YC combinator [13:56] as a visiting partner um that was after [13:58] you left BNB I I remember we recruited [14:00] you and you and I work directly together [14:03] um working on a batch and so we set in [14:05] interviews together we sat in office [14:06] hours we s in group office hours and so [14:08] you've seen it from the other side of YC [14:10] so I just wanted to like reflect on that [14:12] what do you remember from from that [14:14] batch it was Winter 20 that you and I [14:15] worked directly together what are your [14:17] big memories from that yeah I mean I [14:19] remember uh that was well first that was [14:20] the uh like half remote unplan batch [14:23] because it was right at the it's like [14:24] the last weeks right it was like the the [14:27] lockdowns happened cha [14:29] and we had to make some stuff up that's [14:31] correct three it was like two or three [14:32] weeks before demo right at the tail end [14:34] exactly just reflecting we've had some [14:36] great companies just from our our group [14:38] that batch like I think we had yeah like [14:40] 50 or 60 companies and I think the the [14:43] success rate is astronomical um whatnot [14:46] is a multi-billion dollar company airite [14:48] is a unicorn um there's a number of [14:50] other well-known companies that were in [14:51] our group post hog build buddy 99 Manos [14:54] uh Yasser Stark Bank in Brazil pully um [14:57] so it was pH phal Talent um that was in [15:01] our group at least my reflection from [15:03] this was that like how formidable the [15:05] founder really is and like how how much [15:07] they really want to make something work [15:10] maybe not that specific thing maybe [15:11] something else but like make something [15:13] work in the world like is such a [15:15] critical thing that was just a really [15:17] special group of people and they were [15:18] all doing very different ideas very [15:20] different vertical very different types [15:21] of Founders they there wasn't a lot of [15:23] overlap I would argue between who we had [15:25] in that group so yeah we sat in office [15:27] hours together we sat in group office [15:28] hours together we saw all these [15:29] companies at the most nent stages and [15:32] then you know I guess you're a bit of a [15:34] masochist uh and you I remember you [15:36] saying oh you know what I'm just I got [15:37] another company in me I'm gonna go I'm [15:39] going to do a do over um maybe yeah what [15:42] was your thinking on deciding to do [15:45] another startup yeah no I mean it wasn't [15:47] a decision I feel like I had to make you [15:48] know I knew I was after fight car I knew [15:50] I was going to do it again uh and you [15:52] know but this time we'll get to that but [15:54] I was you know we were going to be much [15:55] more thoughtful about it and and I had [15:57] spent a lot of time uh [16:00] working with Lou and getting to know Lou [16:02] uh when my co-founder when we were at [16:03] Airbnb um he was my engineering [16:06] counterpart at the company and and so [16:08] you know we were working on like we' had [16:09] been noodling on ideas and stuff for [16:11] like pretty much two years really until [16:13] we we ended up starting zip so just kind [16:15] of on the side and and we we both [16:17] committed to both quitting basically and [16:20] and kind of going full-time um literally [16:23] March 31st uh 20 2020 so that was right [16:26] after is that funny Tim yeah it's like [16:29] week a few weeks after the lockdowns [16:30] after the lockdown and for Lou it was [16:32] quite a change because I think Airbnb [16:34] Revenue dropped like 95% the week he [16:36] left which was you know quite a change [16:38] for for the company yeah and so uh but [16:42] we were forced to you know be we were [16:45] alone and and kind of in lockdown just [16:47] trying to figure out what we wanted to [16:48] to do it is such a humbling experience [16:50] right because you literally working at [16:52] YC as a visiting P partner you know [16:55] you're meeting all these Founders and [16:56] you know helping people think through [16:58] pivots and and yet you realize like you [17:00] don't know yourself what your idea is [17:02] and what you're going to do and candidly [17:04] zip for us was a mid YC batch pivot uh [17:07] we actually were working on a series of [17:09] different ideas um and I remember uh you [17:13] know we had a really really helpful uh [17:16] come to Jesus office hours with you [17:17] Dalton where you were like guys what are [17:19] you doing uh and uh and you know your [17:22] advice was like you guys know you want [17:24] to start something with execution risk [17:27] but you don't so much want to take on [17:29] Market risk as a as a second time [17:30] founder so why don't you find you know [17:33] an old software company uh that exists [17:36] in the world that you know hasn't like [17:39] hasn't changed much uh in in a long time [17:41] and and sort of figure out like what [17:44] what's changed in that space in the [17:45] world and like and try to solve a new [17:48] problem uh and uh and so we did that and [17:50] that led us to procurement but I have to [17:53] say like you know it was just like that [17:55] CH I mean that changed my the trajectory [17:57] of my wife and that created the company [18:00] uh and that was as a second time YC [18:03] founder after working at YC right and [18:04] like it's just so helpful I would love [18:07] if you could help demystify Enterprise [18:08] sales there's a lot of Founders that [18:10] have a lot of questions about Enterprise [18:12] sales that haven't done it before and [18:14] you're someone that is really good at [18:16] Enterprise sales that has imense scale [18:17] doing it and you went zero to one on it [18:19] it's certainly been a learning [18:20] experience for me and still is right [18:21] because we literally had never worked at [18:23] a company before before uh before zip [18:25] that had a sales team in it but um one [18:29] to your point actually about like your [18:31] time is the most valuable thing you want [18:32] to prove to yourself really that this is [18:34] the right thing to even be investing [18:36] your time into uh we had decided Lou and [18:39] I had decided that the first 10 [18:41] customers that we close we were going to [18:43] try to sell them completely cold like [18:45] through cold LinkedIn Outreach or [18:46] whatever but not referrals not friends [18:49] not anyone we know because if you can [18:51] get 10 different people and 10 different [18:52] companies in the world to you know take [18:55] out their proverbial credit cards and [18:57] buy your thing when they don't owe you [18:59] anything in the world that means like [19:00] you're more likely to have Market fit [19:01] and that's what we wanted to prove uh or [19:03] disprove um and and so that's how we [19:06] like we started out and and we built the [19:09] muscle for outbound which even today [19:11] we're significant majority outbound [19:13] driven business today not inbound and so [19:16] we literally reached out we would max [19:17] out our LinkedIn connections diligently [19:19] every morning and then we would message [19:22] people that add us back because it [19:23] doesn't cost you inails so it's free uh [19:26] and we would just we would just reach [19:27] out and we would ask truthfully [19:29] initially for advice because we wanted [19:31] to learn more about the space and what [19:32] their problems were uh and that was [19:35] helpful I mean in two or three weeks we [19:37] have uh we have a document that has 107 [19:39] pages of notes in it wow uh from all [19:41] these conversations um and that helped [19:43] us sort of cement the idea that we were [19:46] going to work on which is exactly what [19:48] zip still does today uh but it helped us [19:51] then convert that into sales because we [19:53] learn from these folks we took all these [19:55] notes and then we were like oh we should [19:56] do this and we'd go back and say hey [19:58] remember that conversation we had your [20:00] feedback was so helpful to us that we in [20:02] fact we built it can we show it to you [20:04] and then they were like wow that's [20:06] really cool like no one ever does that [20:08] you know for for me and and so and [20:09] that's how we ended up getting people [20:11] excited and closing our our first set of [20:14] of customers but we wanted to we wanted [20:16] to do it totally cold um and step by [20:19] step and how did you price for these [20:21] first customers that's a really common [20:22] question I get well one it is important [20:24] to charge because I've also seen [20:26] Founders that like want to do a design [20:27] partner thing or or you know it's free [20:30] for some reason because they're just as [20:32] a Founder right you're like I have no [20:34] customers or like a few customers I [20:36] don't have confidence in my product like [20:38] how could I possibly charge money for it [20:40] and the truth is like if there's enough [20:41] of a pain and promise of a solution like [20:44] people should and will pay for it and [20:46] it's a test and you want the people to [20:49] pay because you want feedback that [20:51] actually helps your product you don't [20:52] want feedback from people who that who [20:54] would never have otherwise bought it [20:56] potentially uh and so it's really [20:57] important to charge I don't think you [20:59] need to think too much about how much [21:01] you charge you charge maybe 10 grand or [21:02] 20 grand a year or whatever something [21:05] rational that like there's no company [21:08] out there that's a reasonably siiz [21:09] company that can't afford like a 10 [21:11] $20,000 year purchase what if someone's [21:14] thinking wait but I can never charge [21:15] that much my product is bad or I haven't [21:17] built much like how do you overcome that [21:20] what I would say is you'd be surprised [21:22] how much Enterprise software is bad and [21:24] it's not they're not charging 20K [21:26] they're charging like you know Millions [21:28] for first uh and second of all like in [21:30] the big picture like 20K a year like [21:32] just doesn't matter to a company uh [21:34] that's you know that has 100 200 [21:36] employees in it like it really doesn't [21:37] matter and if they're not willing to pay [21:38] that that is telling you something that [21:40] you should be realizing which is you [21:43] know maybe you should work on something [21:44] else or you need to tweak what you're [21:45] building um that's the honest answer and [21:48] over time you can you know as you get [21:49] more confident you can you have more [21:51] referenceable customers you have happy [21:52] customers you can charge more over time [21:56] um but initially just charge enough to [21:58] know that like it's something rational [22:00] there's pain they're willing to pay and [22:02] then just prove that you have something [22:05] my big theme that I feel like I've [22:07] learned working with you and that I [22:09] understand in your whole story is that [22:11] you're a Founder that kind of got to do [22:13] a doover where you had a startup yeah um [22:16] you did the full thing you learned a lot [22:18] you you made incredible progress then [22:21] you had time to go be an employee to be [22:23] a PM then you had time to work at YC and [22:26] see what it's like to to to be a YC [22:28] visit partner and then you got from [22:30] first principles to do a startup again [22:32] and you got to be very intentional in [22:34] every decision you made about what [22:36] things you wanted to keep from your [22:38] experiences and what things you wanted [22:39] to do differently and so to me that's [22:41] that's the big theme here and so I'd [22:43] love your thoughts on you know this [22:45] overall decision-making framework and [22:47] sort of what what are the things that [22:49] you chose to take from your first [22:50] startup that you brought to your second [22:52] one and what the things you're like nope [22:53] don't want to do that again absolutely [22:56] yeah I think if I had to really distill [22:58] it in my personal Reflections um it's [23:01] like you know the first time as a I was [23:03] a first time founder right I I dropped [23:05] out of school like I cared a lot about [23:08] what others thought like I cared what my [23:10] to the point I was just making like what [23:12] my team thought the leaders thought [23:14] right like oh well people quit because [23:15] this person the story executive comes in [23:17] and then leaves I cared what our [23:20] investors really thought right like oh [23:22] like how is the board meeting going to [23:23] go like how do we like paint a positive [23:26] picture about the business and press and [23:29] all this other stuff um not that I cared [23:31] about press but like you know you care [23:32] about like you don't want negative press [23:34] right and so you you care about a lot of [23:36] these things and then the second time [23:38] you really are like you know what it's [23:40] my time I just want to build something [23:42] that people want that like really works [23:44] and so actually now what I'm going to do [23:46] is like try to disprove things like the [23:48] first set of customers like yeah I want [23:50] them to buy cold like I don't just want [23:51] Revenue like I don't care like I want to [23:53] know that this thing is real you know [23:55] and like and like yeah like if we have a [23:57] board meeting which obviously we have [23:59] board meetings like I'd rather we just [24:00] focus on what's broken in the business [24:02] because ultimately that's how we get [24:03] better like I don't want us to spend a [24:05] lot of time talking about what's going [24:06] well cuz that's not going to help us and [24:09] like it's just such a liberating way to [24:11] think about things to just seek truth [24:14] right whether it's your team your [24:15] investors ultimately it has to come from [24:18] you that's awesome well thank you so [24:20] much for joining us today I really [24:21] appreciate it no thanks for having me d [24:25] [Music]