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Gokul Rajaram

@gokulr126k followers

investor () and builder (, , )

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1Apr 15, '23lol154×3.4M44k6.9k2.4k
2Mar 21, '23Many founders who raised large amounts of money ($10m+) in 2020-21 but subsequently realized they don’t have PMF, are going through an excruciating psychological journey right now.75×1.6M2.6k291680
3Sep 6, '23A successful Silicon Valley entrepreneurs told me today that he had no health issues of any kind when he was in the supposedly high stress job of running a fast-growing tech compan63.7×1.4M3.6k252799
4Apr 25, '23How to present In 2006, I helped @ericschmidt create a deck outlining Google’s strategy, for a presentation Eric was delivering to the company. It taught me a profound lesson on ho40.9×892k3.3k4183.7k
5Dec 9, '23Investors and CEOs: The bar for technology companies to go public on US exchanges today is $500M of annualized high margin (75%+ GM) revenue. Klaviyo LTM revenue: $585M (80%+ GM) I28.2×615k82387610
6Jul 5, '23Just spoke with a founder who's shutting down their company. Over the last few years, the company built a handful of products that people oohed and ahhed over (and professed love f25.5×557k1.6k215432
7Mar 8, '231. Barrels and ammunition I didn’t overlap with @KeithRabois at @Square, but when I joined, his precepts were (and still are) all over the company. One of the most powerful metapho25.2×550k73197722
8Feb 10, '231. Founders and CEOs don’t have a good way to think about competitors. Some ignore them, others obsess over them. Neither is optimal. IMO, the right way to evaluate competitors is 23.3×508k1.3k151948
9Mar 17, '23We are seeing the first wave of white collar workers being laid off as a result of AI. Specifically, as law firms adopt AI tools for document processing, they are starting to lay o22.9×500k750103187
10Dec 19, '22Hearing from CPO candidates in the market: many Series B/C companies haven’t yet found PMF despite having raised tens of millions of $. The CEO believes the CPO will help them find21.9×478k1.7k133176
11Nov 9, '24Perpetual dissatisfaction I've now closely worked with/for several founders of $25B+ companies, and one characteristic I've observed in all of them: PERPETUAL DISSATISFACTION WITH 21×458k1k98897
12Sep 12, '23I'm sure every YC class has college dropouts, but this is the first class where I've met multiple teams comprised entirely of freshman CS dropouts from top schools. They all believ20×438k82670232
13Aug 2, '23CHIEF PRODUCT OFFICER HIRING Over the past few years, I've seen several top private tech companies part with their Head of Product / CPO in less than a year. The symptoms are many,18.8×410k56663291
14Jan 30, '24The CEO of one of the best companies I've recently met, has a unique (and I believe compelling) philosophy around hiring: make managers prove themselves as ICs first. "We don't dir18.6×405k1.2k78736
15Nov 21, '23EARNINGS CALLS AND INVESTOR PRESENTATIONS Startup CEOs: one of the highest ROI investments you can make to move forward your understanding of the market you play in, is to read the15.5×338k70870667
16Mar 29, '25SF on Saturday morning: a large % of Waymos are ferrying solo kids (8-14 yo), presumably to sports or other activities. A friend told me that 85% of parents at their kids’ SF schoo14.9×326k2k109365
17Apr 3, '23HBR Case Study from 2025: You’re the founder/CEO of a $75M+ revenue company. You not only have PMF, you are the leading player in your category, a category that you created. You ra13.7×299k63853318
18Feb 1, '23Text from a YC founder in the current batch: “half our batch is doing something with chatGPT”. Is the world ready for 150+ AI startups unveiled on demo day.?13.3×291k63771106
19Mar 10, '23India-based founders don’t know who to turn to as an alternate to SVB. Likely true for founders in other countries too. From what I hear, SVB was the only bank who’d bank a Delawar13.3×289k854102132
20Jul 28, '23CEOs of early stage startups: the most dangerous employees are the “good” ones. The “bad” ones are easy to weed out while the “great” ones clearly stand out. It’s the good employee13.1×286k66364313
21Jul 16, '25Thinking Machines is the fastest growing company in history. No comparison. They've hit $80M ARR in 1 day. Take that, Mercor, Cursor and other contenders!!!!13×283k1.6k47450
22Jul 1, '24A huge % of SaaS companies that were founded ~5-8 years ago and got to $10-50M ARR, are now building and upselling a new AI product to their current customers. This AI product like12.2×267k73172488
23Jun 26, '24hiring and culture at Julian Robertson’s Tiger.11.2×245k91231494
24Apr 20, '220. Startup CEOs: if you want to hire the leader for a particular function, follow this playbook.10.6×02.8k3632.7k
25Sep 10, '24ENTERPRISE SAAS STICKINESS - WHAT STICKINESS? This news from @Klarna should have every enterprise SaaS company shaking in their boots. If an internal team using AI can replicate 2010.5×230k841127801
26Mar 10, '23Important to note that SVB’s loan book (their assets) are quite good. They hold a ton of securities. They just didn’t have enough cash to meet withdrawal demands, and when that hap10.2×223k7386368
27Sep 1, '23Series A founder: Our revenue is 3x what we were a year ago, with 0.5x the burn. I cut everything that was not essential, and took a first principles approach to every expense and 10.2×222k65147238
28Feb 23, '24HOW TO BUILD A HIGH PERFORMANCE CULTURE Every CEO and leader wants to build a high performance culture. To do this, you need to be intentional about 3 things: managing out low perf9.8×214k650901.1k
29Aug 9, '23I love working with people younger than me. At Google, I was the same age as my colleagues. At Facebook, I was ~10 years older. At Square, ~15 years older. And I just learnt that o9.7×212k1.1k67131
30Jul 31, '23Every Internet / software company I've spoken with, is aiming for profitability much faster / earlier than they would have 1-2 years ago. In many cases, this means getting to cash 9.5×208k63359291
31May 8, '23Hiring an over-senior leader Just met the founder of a series A company who is having challenges with their VP Sales. The Vp Sales is a super senior leader with great experiences. 9.5×207k65861227
32Jul 28, '24CHARGE 5-25X MORE FOR YOUR CONSUMER SUBSCRIPTION PRODUCT Consumer CEOs: Charging $20 monthly / $200 annually for your product means that you need 1M subscribers to get to $200M ARR9.4×206k58039905
33Apr 12, '25ENTERPRISE AI: BUILD AGENTS, NOT TOOLS In the past 2 weeks, I've met several AI agent tooling startups that have each realized that the biggest problem in large enterprises is NOT 9.4×204k842851.1k
34Aug 1, '25CREDENTIALS DON’T MATTER Over the last few months, I’ve seen several A+ execs and operators flounder and fail at AI startups, while young “inexperienced” builders have crushed exec9.1×200k1k128626
35Mar 16, '25COMPOUND OR DIE Five years ago, doing a compound startup was the domain of repeat entrepreneurs who could raise tons of capital, and was otherwise discouraged by investors and advi9.0×196k67571503
36Oct 21, '23CEOs: if you ignore seemingly minor issues, it sends a signal to employees that you are OK with the problematic behaviors manifested in the issue. This leads to the behavior becomi8.7×190k71468283
37Feb 21, '25Just heard of a law firm that fired their legal AI vendor after they missed a court date for a $100m case. In several verticals like law, health, etc, accuracy of the AI tool is no8.1×177k1.4k95346
38Dec 11, '23Met a pre-revenue AI startup doing a secondary as part of their seed round. Had to double check my calendar to see if it's 2021 again.7.3×160k6242361
39Oct 13, '23BOARD MEMBERS A founder with multiple VC partners on their board told me that their favorite board member is the one who doesn’t panic and start asking “omg what’s going to happen 7.2×158k59871147
40Jan 12, '23As a startup employee, your hope should be that if your company fails, it does so quickly, within 6-12 months, versus slowly and painfully over multiple years. The opportunity cost6.9×152k8625988
41Feb 17, '21Founders: One of the best startup hacks I've seen is hiring a smart generalist to own the numerous random yet critical projects that need an owner. From sourcing talent to creating6.7×03.5k412589
43Oct 10, '24Just heard from a friend who’s been at a FAANG for the past few years: “we are in a much better financial standpoint than before joining them”. This statement underscores a basic t5.9×129k77122293
44Jan 12, '23Canadian friend: "JP Morgan did more diligence on me for a $2k limit credit card as a Canadian immigrant than they did for a $175M acquisition."5.8×127k98210932
45Feb 5, '24Enterprise-focused seed founder, upon finally receiving a reply after 8 weeks of non-stop following up with the decision maker: “I’ve learned that I just need to email every week u5.8×126k63044290
46May 6, '221. I have been trying to find the best "first question" to ask a startup when I meet with them. After many iterations, I think I have it. Here it is, and here's why it works.5.4×01.8k2201.2k
47Jul 18, '210. CEOs, CPOs and VPEs: The core product team has traditionally been a triad: Engineer, Designer, PM. Consider changing this to a quartet by adding Analyst. Product analysts can tr5.3×02.2k276859
48Mar 9, '25PREDICTION One or both of @canva and @figma will enter the AI builder market in the next few months, likely with a product very similar to @boltdotnew or @lovable but tightly integ5.3×115k79344354
49Jan 9, '25I'm excited to launch @MarathonMP with my friend @MBGilroy. Marathon will invest in and support founders who are obsessed with the problem they're solving, who understand the custo5.1×111k7272285
50Jun 19, '25SELL BEFORE BUILDING I've now seen multiple episodes where PMs have used vibecoded / no-code prototypes to get 2-5 customers to sign LOIs or even contracts, and then use this "proo4.9×108k61453465
51Feb 19, '19Friend: “I know this guy who gets driven from Atherton to SF every day.” Me: “That’s not uncommon.” Friend: “He gets driven in a van, and the back of the van is set up with a @onep4.7×02.7k31738
52Jun 14, '24Kathy Xu, one of China’s top venture investors (eg: she led JD’s Series A in 2007) counts Kanye West’s mom as one of her top formative influences while studying at Nanjing Universi4.5×99k56671190
53Nov 2, '25AI founder talking about why it's so hard to hire in SF today: "in SF, the AI labs have tremendously skewed engineers' perspectives. Every engineer either wants a package that is a4.3×94k73715179
54Aug 10, '24I am still numb and trying to process Susan's passing. It is an unimaginable tragedy because it just seems wrong for such a truly GOOD person to be taken away so early. Google woul4.2×92k6332174
55Mar 10, '22CEOs and founders: here’s an example of how to convince candidates to look past titles. Read this email I received from a Series A founder today who was in the same dilemma:3.6×01.1k142796
56Nov 30, '24Enterprise pricing: Have MULTIPLE leverage points to use when negotiating. Founders: the conventional wisdom around pricing your product is to keep it simple. Unfortunately this wo3.5×77k58634711
57Sep 12, '25What @rabois calls barrels, Slootman calls drivers. Critical to hire as many of this archetype as possible.3.3×72k63052475
58Apr 10, '21$1m ARR co. Tried to raise bridge round at $30m cap. Little interest. Changed “bridge” to “pre Series A”, raised cap to $60m, waited a month to ensure metrics still strong, went to3.2×01.9k150252
59Feb 20, '21Why do some founders raise at 500m with 0 revenue while others struggle to raise with 10m revenue? Fundraising is about NARRATIVE, not just NUMBERS. Narrative includes a compelling2.9×01.5k166269
60Jul 29, '22Early stage B2B Founders: If you have to choose between one very large first customer (say $500k+ ACV) and ten smaller first customers (say $50k ACV each), the right choice (at lea2.9×01.2k141424
61Aug 6, '25Brilliant tactic from Frank Slootman to raise standards: Ask people what they think of their own work.2.9×62k63343563
62Mar 29, '20Top venture investor: "We are cutting all valuations by 50%. And a flat round is the new 3x up." This is what most startups have to look forward to over the next few quarters. Brac2.8×01.5k278114
63Jun 11, '21Rule of 30: startups often give up on fundraising too early. You need to meet at least thirty investors before you can conclude that your fundraising is not successful. Remember, y2.6×01.4k211184
64Feb 7, '21Every leadership role is part clouds (strategizing, inspiring, vision) and part dirt (doing, executing, details). People who go into a leadership role expecting 100% clouds will fa2.5×01.4k209156
65Jan 12, '21The “what’s your moat?” question for early stage companies ignores the fact that if a one year old company can build a moat, it’s NOT a real or deep moat. Real defensibility take s2.5×01.6k133121
66Oct 27, '21Entrepreneurs and operators: the best memos and decks are written in the form of a conclusion followed by a series of assertions supporting the conclusion.2.4×087069525
67Dec 9, '20Seeing a small number of founders start to move away from pitch decks and instead use long form memos to describe their product / biz. These docs show clarity of thought and allow 2.4×01.5k66147
68Aug 1, '21CEOs: When communicating a decision to your team, pls talk to 3 things: (a) who made the decision and who was consulted (b) guiding principles (c) alternatives considered Even if y2.4×01.3k120299
69Jul 19, '21Strategy and org structure are inextricably tied together. If your org structure is not aligned with your strategy, you will fail. Trivial example: if there is no Directly Responsi2.3×01.1k105288
70Nov 24, '21Startup CEOs: if you haven’t yet done so, please make a list of the top 10 strategic partners / acquirers in your space and use your investors / advisors to get intros to a C-level2.0×01k98268
72Sep 7, '22Startups: if you hear an eng hire spending too much time talking about how to scale things, likely not a good fit. Early startups are about speed of iteration, not scale. Every gre1.9×01.1k124143
73Jun 28, '22I had to raise a financing round for my startup in mid 2009, a few months after the collapse of Lehman and right in the midst of the global financial crisis. A few lessons:1.9×0659101367
74Jan 16, '21Startups: instead of rushing to add someone to your board, consider making them an advisor for 6-12 months. Do you enjoy working with them and trust their advice? Do your execs fee1.8×01.1k14294
75Aug 5, '21CEOs: The best functional leaders (legal, finance, marketing, etc) are businesspeople first, functional specialists second. Evaluate candidates through the lens of how they can use1.7×0818109204
76Jul 29, '21Founders: please don’t give a VP title to anyone before you get to 100 people. I’ve lost count of how many founders I counsel on how to “deal with” VPs that they hired too early.1.7×075276219
77Oct 10, '21This LinkedIn/resume inflation, while funny, is why hiring in startups is so difficult. And it’s so important to “hire slow and fire fast” versus the inverse.1.7×01k10368
78Sep 29, '22Founder: “We want to do some quick customer discovery by showing customers mocks and asking them what they think.” NO. Customer discovery should be used to uncover customer problem1.5×078065156
79Apr 9, '20Most startups are focused on defense today: cutting costs / extending runway. However, surviving the crisis doesn't mean you'll thrive once it's over. The companies that win will a1.4×076613660
80Sep 16, '21Entrepreneurs: please remember that it’s the slope (growth rate) and quality (margin, retention) of revenue that drives valuation multiples, as much as - or more than - the quantit1.4×063083199
81Nov 22, '22Convos with mid stage founders in the past week. Founder 1: exited 2 engineers in 1 day. Founder 2: mandated back to office last week. Founder 3: actively starting to track/measure1.3×07265989
82Dec 15, '21CEOs: It’s important to have a cordial relationship with the CEOs of your competitors and to meet with them on a regular basis. Why? Three reasons, which ultimately all boil down t1.3×069260139
83Oct 5, '211M ARR growing to 3M ARR in 12 months is no longer top decile for startups. It's 1M to 5M in 12 months. Everything is being reset at a higher level, including growth rates.1.3×074760106
84May 20, '21Cash flow >>>> Revenue.1.3×09514423
85Apr 23, '21CEOs: if your marketing team says your company has a strong brand, ask to see how this strength manifests itself. A strong brand should lead to: lower cost of customer acquisition 1.2×066910480
86May 27, '20ByteDance revenues 2018: $7.4B 2019: $17B (129% YoY) FB revenues 2013: $7.9B 2014: $12.5B (58% YoY) 2015: $17.9B (43% YoY) Not that it's a secret, but ByteDance is on an incredible1.2×072810531
87Sep 22, '22Startups: Resist the urge to pursue channel partners early. No channel partner will engage with you unless you’ve (at least) hit PMF and they see/hear of shared customers using and1.2×066653102
88Jun 18, '21Spoke with a friend at a ~$X00B pension fund who just made a direct investment in a pre-launch company. Spoke with a friend at a “seed” fund who put together a $100m SPV into a pre1.2×07455855
89Oct 30, '21Someone sent me this quote from @jack. The lessons I learnt from him are numerous, but a powerful one was that great design and great products are more about subtraction than about1.2×060071134
90May 15, '21I’m always awed by the times kept by entrepreneurs in India and SEA. I routinely do calls with them at 1-3am their time, and invariably find them energetic and fresh. I have to ass1.2×07773335
91Aug 30, '21New user onboarding and activation is one of the most critical things for teams to test. Unfortunately it’s also one of the hardest, since people don’t go though the NUX flow more 1.1×059361114
92Sep 6, '22C-level execs: when you first join a company, don't be surprised or discouraged if you are initially micromanaged by the CEO, especially if that function didn't exist earlier. As a1.1×061751116
93Aug 20, '21It's very painful on iOS to not be able to "unread" text messages. Once I read a text message, I need to reply right away, or I risk forgetting about it. So now I just don't read a1.1×07702013
94Nov 11, '21I met a strong company today that's raising $10M from a Tier 1 investor. I asked the CEO why they aren't raising more. Best answer ever:"Our burn has historically been very low; at1.1×06934358
95Mar 22, '19I increasingly think of @a16z as a marketing and content firm that monetizes through venture capital. Their content marketing is as good as - or better than - that of any best-of-b1.0×07135233
96Apr 4, '20Top 2 characteristics of successful execs at any company: (a) get s*it done (b) great people judgment. That’s it. That’s what CEOs want in their execs. Across every function.1.0×05706188
97Jul 31, '20Sign of the times: a stealth startup did a podcast to try to recruit software engineers. The ration of investors to engineers reaching out to them (as a result of the podcast) was 0.9×05784825
98Jan 16, '25My friend @rob (cofounder of @Ro) is the best person to go to when you need a need a hard-to-find domain name. is awesome. Getting the .com is a big milestone for most startups!0.9×19k1.2k581.4k
99Oct 17, '20I've now served on ~10 private and public boards over the past 12 yrs. 2 observations:(a)Founders are much more assertive today; a decade ago, investors dominated board meetings.(b0.8×05731738
100Aug 3, '19My kids upon hearing that @DoorDash and @Caviar are joining forces: “Finally, we don’t need to feel guilty while using DoorDash because our dad works at Caviar”. 😂0.7×0576103
101Oct 16New post on @signalfulnews @shaneparrish interview with @BillAckman. Signalful summaries going forward will have more insights and more detail per insight. Check it out, and subscr0.2×5.1k17321

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