The Ledger

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Disclosure
Cakir let go 50 people after automating manual scraping with Clay
“I've kind of let go about 50 people. And that's because we got a tool called clay, you know and suddenly we didn't have to do manual scraping and we didn't have to do manual copy paste from LinkedIn and so on.”
Tim Cakir Jan 20, 2026 ▶ 8:02 He Let Go of 50 People After One Tool Changed Everything
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Barr: Most founders should bootstrap or raise from angels rather than VCs
“And I'm a VC and I don't recommend a lot of people go VC. I do recommend people go bootstrap, or if you're not going to bootstrap and you want a little bit of money, go angel.”
Jeremy Barr Dec 5, 2023 ▶ 26:25 Turn Your Self Audio Down and Watch Everything Change
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Weisbrot: VC power-law investing is just bad money management hiding failure
“I have heard some of those ideas that you just assume most of the companies are going to fail. And I feel like that's just bad, like money management being kind of swept under the rug. So that's why I like to do angel investing because I'm going to do everythi…”
Sean Weisbrot Dec 5, 2023 ▶ 31:22 Turn Your Self Audio Down and Watch Everything Change
Disclosure
Weisbrot: Singapore entity avoids hiring citizens to bypass local taxes
“We don't hire any Singaporean citizens, even though we're a Singaporean entity. So we can avoid a lot of the extra taxation and requirements that the government places on a company that hires a local citizen.”
Sean Weisbrot Mar 20, 2021 ▶ 18:08 France's Two-Tier System: The 1% Pay No Taxes Legally
Disclosure
Gupta: Consultants must walk away from failing engagements by week two
“No one in the company is allowed to drag to six weeks just to make a point that we are trying to do something. No, we walk out.”
Saurabh Gupta Aug 18, 2026 ▶ 4:03 3,000 Tools and Enterprises Only Use 15% of Them
Disclosure
Narasin remains underwater on Surf Air after a cram-down by 'bad people'
“I was in their first investment round, and I'm still underwater on the public company. It's ridiculous. Because of a bad round done by bad people, in my view that crammed me down even though it was an upfront.”
Ben Narasin Jul 14, 2026 ▶ 2:47 Happiness Found Him Through a Crappy Movie at 2AM
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Narasin passed on Oura Ring because Will Smith and Prince Andrew led
“I almost invested in the first round. Interestingly, it was the round that ended up being led by Prince Andrew and the Fresh Prince of Bel Air, Will Smith, and I was like, I'm not paying Prince prices. These people are amateurs. I don't know what they're doing…”
Ben Narasin Jul 14, 2026 ▶ 30:01 Happiness Found Him Through a Crappy Movie at 2AM
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Weisbrot: Laid off designer because AI creates better thumbnails in a minute
“I had a designer and the AI is able to produce better work than the designer faster and cheaper. Like, you know, it used to cost It used to take three days to get a thumbnail back. The AI can do it in a minute, and it's better quality. And so I had to let the …”
Sean Weisbrot Jun 23, 2026 ▶ 15:26 60 Days Down to 60 Minutes Changed How Shelton Thinks About His Own Team
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Millar: Refusing the COVID-19 vaccine ended my acting career
“Walking away from acting because I didn't want to take the COVID shot was a very painful decision, but it didn't feel like a decision.”
Helen Millar Apr 7, 2026 ▶ 17:18 There Is Always A Gift In The Grit
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Wehn: Our AI Startup Charges 15-25% of Customers' Created Annual Value
“And if we say, Hey, we think that value is a million a year. Our price tag is somewhere between 15 and 25% of that as an annual license. So 150 K to 250 K to generate a million in annual value.”
Philipp Wehn Feb 10, 2026 ▶ 4:55 Why Raising $15M Made Him Want to Do Less, Not More
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Cakir replaced traditional CRMs with local Markdown files and Claude
“I don't have a CRM anymore. My CRM is Markdown files on my computer, right?”
Tim Cakir Jan 20, 2026 ▶ 25:14 He Let Go of 50 People After One Tool Changed Everything
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Ethan Monkhouse maps unbuilt products by assuming external tech releases within weeks
“We don't plan, we plan for people to build things in our roadmap. We have tech that we don't know how to build. We don't know who's going to build it, and it doesn't exist right now, but we know in eight weeks time, someone's going to build it. We don't know w…”
Ethan Monkhouse Oct 27, 2025 ▶ 25:31 Your LinkedIn Profile Is Not a Profile. It Is a Landing Page.
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Spahr: Refused thousands of dollars to write paid Forbes contributor articles
“I've been a contributor for Forbes and for others, and I've been asked to do a story for a couple thousand dollars on X, Y, or Z. Now I refused”
Curtis Spahr Aug 26, 2025 ▶ 3:43 Earned Media Is Still King, But Not for the Reason You Think
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Kwan: Four15 Digital's Core Value Now Prioritizes Employees Over Clients
“One of our values is now if we have to choose its employee over client.”
Borja Kwan Aug 19, 2025 ▶ 10:20 He Fell on His Sword in Front of 20 Employees and It Worked
Disclosure
Weisbrot: Investors were half the reason my previous software business failed
“I could very easily launch another software brand, but I've learned the lesson that I don't want investors in my life because investors were half of the reason why my business failed.”
Sean Weisbrot Aug 15, 2025 ▶ 19:25 Your Business Isn't Stagnating, Your Mindset Is (Live Coaching)
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Weisbrot: Stopped using Lovable due to severe hallucinations and broken routes
“This was a big reason why I was using lovable before and I got away from lovable because it was hallucinating. The deeper into the project, the more it hallucinated to the point that it was rewriting UI. It was removing pages from the route configuration.”
Sean Weisbrot May 30, 2025 ▶ 24:43 Why Founders Stopped Being the Human in the Loop
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Nanavati: Cimphony considers itself a service company, not a software company
“We're not a software company. We're a service company is what I say.”
Arpan Nanavati May 30, 2025 ▶ 25:34 Why Founders Stopped Being the Human in the Loop
Disclosure
Wang walked away from a $50M acquisition offer out of fear
“At one point in time, there was about fifty million dollars. And I chickened out. Like I chickened out. I blame it on my dad getting, getting sick at the time. Right. Right now. I have an official storyline that I tell myself at the time my dad was sick. So I …”
Zee Wang May 27, 2025 ▶ 21:50 Count On Other People Being Lazier Than You
Disclosure
Weisbrot: Enforcing personal guarantee against founder who lost invested capital
“Another one failed immediately out of the gate because they got scammed by a service partner and lost all of the capital, so there's a personal guarantee on the CEO I'm trying to get back now that I made him sign because it was, there was a little bit of risk …”
Sean Weisbrot Mar 19, 2025 ▶ 2:44 Cash Business vs. Wealth Business: Most Founders Mix Them Up
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Bimani: BPS Security Built Proprietary Software to Avoid SaaS Subscription Fees
“We hired a developer to do all our software. So we have our own custom software for the company. So we only have to pay for the maintenance on it instead of paying a subscription fee to someone else like Soho or a CRM provider or something like that.”
Glenn Bimani May 7, 2024 ▶ 10:57 He Gave Them the Dollar They Asked For, Then Walked Away
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Weisbrot: Salaried Team Members Can Moonlight Once Weekly Tasks Are Completed
“Every week you have stuff that you commit to doing, if you commit to doing that stuff and you still have extra time, that's your time, right? I'm not going to tell you what to do at that time. If you work with somebody else, that's your time.”
Sean Weisbrot May 7, 2024 ▶ 19:47 He Gave Them the Dollar They Asked For, Then Walked Away
Disclosure
Saxena prioritizes BetterCommerce employees over customers in his business philosophy
“Customers are always very important. But the people that work with you, I put them at a higher, you know, pedestal.”
Vikram Saxena Mar 22, 2024 ▶ 30:57 Golf at 5:30am in the Dark Changed Everything About How He Runs His Company
Disclosure
Preisinger: WriterGirl runs on a cultural rather than financial balance sheet
“I don't really look at my business through the lens of a balance sheet. I mean, of course I look at a balance sheet, but I look at it through the lens of a cultural balance sheet.”
Christy Preisinger Mar 6, 2024 ▶ 37:07 She Runs on a Cultural Balance Sheet Instead of a Financial One
Disclosure
Finley operates his relationship on renewable six-month commitment contracts
“We actually do an every six months, like, check in. And it's basically, like, we're committed to the relationship for that, those six months, and, like, at that six month mark, we determine whether we want to continue on for another six months.”
Don Finley Dec 12, 2023 ▶ 19:40 His Six-Month Relationship Contract Actually Works
Disclosure
Weisbrot replaced video editor with Opus, creating 15 clips in 10 minutes
“I used to have a guy, unfortunately, I let him go because Opus makes him unnecessary. I was paying him, it would take him about a Two or three hours to make a short. And now I get 15 in 10 minutes.”
Sean Weisbrot May 30, 2023 ▶ 26:11 3,000 Client Q&As Fed Into One Bot That Answers Like Him
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Lassman: Quantum Star Systems Is Developing Parallel Universe Programming Techniques
“That's actually a core part of the innovations that our company, the quantum star systems is, is innovating is that That multiversal or the multidimensional parallel programming techniques, like what has to happen to be able to program using parallel universe…”
Jeremy Lassman May 25, 2023 ▶ 14:21 Passion Is the Fuel, Not the Emotion: One Founder's Case for a New Industry
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De Jong: Co-founder attempted hostile buyout at the eleventh hour
“And on the 11th hour, literally after they had their board meeting to decide on this, my co-founder said, Although, I don't know if I still want to do this. I don't think I want to go through with this deal, and as a matter of fact, surprise, surprise, I have …”
Aldo De Jong May 9, 2023 ▶ 7:43 He Called It a Work Husband. Then Came the Surprise Money.
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Rakshit: ShopFlo avoids formal company culture until reaching larger scale
“We also don't worry about culture a lot, to be honest, at least at this scale. We've realized that we are not reached a scale where We have a stronger culture than a person who would bring it.”
Ishan Rakshit Apr 5, 2023 ▶ 32:59 He Joined VC With No Plan to Stay - Here Is What He Was Really After
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MIT45 to cap full-time workday at 6.5 hours by Q4 2023
“By quarter four of 20, 23, no one will be able to work more than six and a half hours a day, but it's deemed full time work.”
Ryan Niedel Feb 1, 2023 ▶ 46:06 Every New Level Has a New Devil - He Proved It From $5M to $75M
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Lindemann: 12 candidates rejected a client's job offers over one toxic manager
“We've gotten to the final interview and they say, I love the company. I love what they're doing. I love the role, but I cannot work for that manager. And I think that's probably about 12, 12 or so people that have, you know, provided that feedback this year fr…”
Travis Lindemann Nov 1, 2022 ▶ 26:31 12 Candidates Refused the Job Because of One Person on Their Team
Disclosure
Druckman: Scrum engagements failed most often with excessively funded clients
“When I think about clients who I taught Scrum to Where I felt like it, they didn't get a lot of positive results from it, or at least not as much as I wanted them to. Very often they were clients that had the problem of having too much money.”
Angela Druckman Jul 26, 2022 ▶ 14:44 Infinite Money Made Her Client Worse at Shipping Than Startups
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Mikic: Flow Ninja mandates in-office work for new hires' first three months
“On our side, we usually have people for the first three months mandatory to be in the office. So they meet everybody who's at that point in the office and just kind of meet the team and can become that much more bonded to the company. And then when they know e…”
Uros Mikic Jun 30, 2022 ▶ 46:03 Webflow Calls Itself No-Code But Here Is What They Leave Out
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Lakritz Raised A $15M Pre-Seed Round Without Writing Any Code
“So, you know, you look at us at anchor, we raised fifteen million dollars in the pre-seed with customer discovery.”
Rom Lakritz May 4, 2022 ▶ 12:11 Rom Raised $15M Before Writing a Single Line of Product Code
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Strauss: Psychedelics bridged the emotional integration gap where talk therapy failed
“Psychedelics were really the only tool that I found that even when it came to therapy and talking with sort of professionals in that regard, you know, there was always a disconnect between, you know, what I was hearing and what I was being shown and my ability…”
Tyler Strauss Mar 8, 2022 ▶ 6:36 Your Brain Has Only 3% of Its Vision in Focus Right Now
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Laker: Chameleon Collective operates as a decentralized holacracy without traditional hierarchy
“We effectively are a decentralized organization. We have a, you know, unique way that we all work together that's allowed us to scale. You know, for example, we have no hierarchy. We use a derivative of management style called holacracy, and we reorg our leade…”
Freddie Laker Sep 16, 2021 ▶ 17:47 The Secret PE Firms Pay $2M/Month For: Nail The Basics
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Stancil: Mode will sacrifice business growth to hire diverse teams
“And so hiring a more diverse team is more effort. It takes time. It is more expensive. But if you value that, then great. And like we do, and that is a thing that I'm willing to say Moog will sacrifice some growth as a business to be able to do that.”
Ben Stancil Jun 22, 2021 ▶ 19:13 The $1.2B Yammer Exit That Funded an $80M Company
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Podolsky poaches top employees from his existing companies for new ones
“I actually, as I grow my businesses, I've known to poach good people from old company to build a new company.”
Michael Podolsky Mar 30, 2021 ▶ 16:00 The Thank-You Letter Trick That Shook 10 Top Managers
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Robinson: GetEmails is not a 10-year business due to legal uncertainty
“Like even right now, for me, I know that this get emails thing is not my end all be all. There's a lot of reasons. I don't want to be in this business for like 10 years. One, the legal aspect is very unclear. You know, it's only legal in the U S like, I don't …”
Adam Robinson Jan 22, 2021 ▶ 37:32 $3M in 12 Months With 5 Employees — Here's the Model
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Halasnik secretly moonlit at Xerox for 18 months to build a startup
“What I did with Xerox, I worked for a year and a half for Xerox, half a day without them knowing it. And then the other half a day, I started my company.”
Steven Halasnik Dec 22, 2020 ▶ 4:32 The Chess Board Secret: Why Small Businesses Only Have One Move
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Weisbrot: Claude codebase access enables testing new software features within an hour
“Claude is helping me to build the software. So Claude can see every file in, in my software code. It can read everything from the repository. So there's no reason to not go, hey, Claude, I just had a demo, and the person gave me three things of feedback. What …”
Sean Weisbrot Aug 25, 2026 ▶ 21:14 Would You Rather Be a CEO or COO?
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Todd Anthony: Pinwheel hires staff laid off by its own clients
“We've actually hired some of those people that have been laid off from our clients. And that has turned out to be an incredibly smart move, if I do say so and has really helped us a lot.”
Todd Anthony Aug 11, 2026 ▶ 3:20 AI Is a Block of Clay and Most Founders Never Sculpt It
Disclosure
Weisbrot Claims He Built Three Commercializable Agentic AI Products in One Month
“Like in, in the last month, I've literally created three different softwares that could all be commercialized and they're all agentic.”
Sean Weisbrot Jul 28, 2026 ▶ 11:42 His Grandpa Worked Until 90 and Changed How He Sees Aging
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Meiring: New AI features are tested with sales prospects before existing clients
“Our first release is into sales. It's not into existing customers. It's actually into sales and go and put this out there and get some feedback and some perspective on how's this resonating with the prospect, right?”
Ray Meiring Jul 21, 2026 ▶ 5:20 80% of the Workload Done Before a Human Touches It
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Mercer: Activate Uses Generative AI to Rank and Validate City Initiatives
“We've built a AI tech enabled platform that creates outcome intelligence. And so activate becomes not just that one day and then 100 leaders. We now have some permanence because we've provided some actual data of the cities that we've had these ideations in cr…”
Shelton Mercer Jun 23, 2026 ▶ 8:33 60 Days Down to 60 Minutes Changed How Shelton Thinks About His Own Team
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Ebstein: Real Estate Professional Status Generated Massive Active Income Tax Savings
“Then, and if you have a spouse that's doing that, or one of you are doing, is doing that, then you can take the depreciation losses from the real estate against your active income when you follow those returns. So that's resulted in probably millions of dollar…”
Ephraim Ebstein May 19, 2026 ▶ 34:07 His Former Boss Later Became His Employee
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Weisbrot: Non-Technical Founder Built Financial SaaS Prototype Using Claude
“And so I worked with Claude and I built this software myself as a non-technical founder, but having experience with a previous company that I had started, I understood what my team was doing then. So I knew, okay, there's a backend, there's a front end, there'…”
Sean Weisbrot May 5, 2026 ▶ 13:32 Why Credible Investors Are Actually Killing Startups
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May: Acquirer failed at shifting his startup's product to channel sales
“I mean, this happened with the company that bought my company. They were very channel sales centric. I didn't think it would work well for our product. And they tried to move us over and after a year they had to switch back to direct, but like their philosophy…”
Rob May Apr 10, 2026 ▶ 8:45 Why the 7th Biggest Player in a Huge Market Beats the Winner in a Small One
Disclosure
Levin expects to invest in fewer true pre-revenue seed deals going forward
“Probably a smaller percentage of the deals I invest in going forward are going to be real true pre-revenue deals.”
Ron Levin Mar 17, 2026 ▶ 22:33 Why the Co-Founder Who Stayed CEO Was the Right Call
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