The Ledger

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Disclosure
Yaman made under $10M in personal liquidity despite Boxed raising $380M
“Yeah, it was not the case.”
Jared Gaiman Feb 26, 2026 ▶ 11:31 From $187M Ecommerce to $5M ARR SaaS: Spresso's Post-Bankruptcy Pivot to Enterprise Software | Jared Yaman
Disclosure
Latka pitches Spiegel a live $5M credit line with no warrants
“My offer, just so you have in the back of your head, we would do a five million dollar line of credit with somebody like you. That's under 60% leverage against your ARR, 50% leverage against your ARR. It's a line of credit. So it can sit there and you pay noth…”
Nathan Latka Feb 4, 2026 ▶ 22:30 How to Scale to $12M ARR: The Serial Founder Playbook for Vertical SaaS and Agentic AI
Disclosure
Walker sold secondary Astronomer shares during Series B and C rounds
“I was offered a chance to sell my shares in secondary at our Series B, Series C rounds. You know, that was, this was the Zerp era, and I said yes.”
Ry Walker Aug 8, 2025 ▶ 3:19 Woah! Unicorn Founder Quits Unicorn During $213M Raise, Launches Something Bigger
Disclosure
Latka: AI search plummeted organic clicks by 50% despite soaring impressions
“And now with AI results, we're showing up in more impressions, 190 K a day, but our clicks have gone down by about 50% on average per day.”
Nathan Latka Jun 12, 2025 ▶ 25:09 Bootstrapper Hits $3.5m, 0 Team Members using new 3x Growth Formula
Disclosure
Zitoun: Submagic offers a 30% lifetime recurring affiliate commission
“We give 30% revenue on the lifetime value of the customers.”
David Zitoun Jun 10, 2025 ▶ 14:19 How I Built my AI Tool SubMagic to $667k/Month With a Tiny Team and No Funding
Disclosure
Yampolskiy: SecurityScorecard Uses Former Jobs Coach to Screen VP Hires
“We actually have a psychologist who interviews, he used to be a coach to Steve Jobs, actually, and Larry Ellison, but he interviews every VP higher and above, and I get a forty-page report on what is a person like, not like, culture, curiosity”
Alex Yampolskiy Jan 7, 2025 ▶ 12:54 3 Strategies I Used To Scale SecurityScorecard to $70M ARR, 1,700 Customers, & $200M in Cash
Disclosure
Liwer: Coro Founders Received Equity Top-Ups Across Funding Rounds
“So there were top ops along the way. Because it's important to the investors to make sure that the founders stay very engaged, and that's the way a smart investor thinks.”
Dror Liwer Oct 31, 2024 ▶ 12:05 His cap table will shock you. $100m revenue, $750m valuation in his series D with Coro Co-Founder Dror Liwer
Disclosure
Moah: Boomerang issues dividends to employees, investors, and founders
“So we have issued dividends for all our shareholders, employees, Investors. Founders.”
Aye Moah Oct 22, 2024 ▶ 25:23 She invented Gmail Send Later in 2010. Bootstrapping to $10m revenue with Boomerang CEO Aye Moah
Disclosure
RB2B experiences brutal 10% monthly churn and a nine-month customer LTV
“Like, 10% a month. It's, we just had an agency, like, cancel 80 accounts and put them under one account, so it looks like it's even worse than 10% a month, but like, it's like a nine month LTV.”
Adam Robinson Oct 17, 2024 ▶ 12:46 Adam Robinson Shares Profit and Loss, $22m Revenue, Strategy behind Linkedin and Lawsuit
Disclosure
Omnisend CEO: Google penalized our experimental fully AI-written website to zero
“We had one experimental branch of website, which was a full AI written. It just got down to zero. No results at all. Like, penalized to zero.”
Rytis Lauris Oct 15, 2024 ▶ 19:02 Genius SEO Hacks This 34 Year Old Used to Bootstrap to $55m Revenue with Omnisend CEO Rytis Lauris
Disclosure
Founderpath Conditioned Financing on Creating a New Management ESOP Pool
“We basically said, Hey, look, we'll fund the business with a million or million and a half or whatever it is. But at the funding date, we also need to see a board resolution that establishes a new, 1015, whatever it was ESOP pool and a chunk of that ESOP pool …”
Nathan Latka Oct 3, 2024 ▶ 18:24 Founder Raises $750k From Founderpath and Increases Equity. CEO Shares how Founderpath Worked for Him.
Disclosure
Schumacher: SaaS Group funds deals from balance sheet, currently 100% debt
“We have tons of cash. We're just doing every deals, doing deals all hundred percent debt. So we're not, because we're not putting things into SPVs or special purpose vehicle. We're not a PE company. We're really just always, always investing from our own balan…”
Tim Schumacher Aug 29, 2024 ▶ 20:06 The Micro PE Playbook: They Bought 20 SaaS Companies, $60m ARR, 300 people
Disclosure
Flodesk refuses to entertain acquisition offers to stay independent
“We, you know what, we've been very we've been very disciplined about not entertaining the offers that have come so far just because they haven't made sense for us. Not even, we have, so we've never even gotten to the point where we've had the discussions about…”
Rebecca Shostak Aug 15, 2024 ▶ 34:56 Genius Affiliate Strategy Helps Bootstrapper Hit $27,000,000 Revenue
Disclosure
Owner.com fires bottom-ranked sales reps even if they near quota
“I move people out of the business that are, like, pretty close to quota. Like, they could be okay performers. I'll still exit them from the business if they're consistently at the bottom of the stack rank.”
Kyle Norton Aug 1, 2024 ▶ 18:35 $5m in ARR? Your CRO Should Be Focused on These 3 Things
Disclosure
Wing Assistant triggered Google conversions using secret chat keywords
“Whenever The word beautiful would show up in the chat window. We would actually trigger a conversion.”
Roland Polzin Jul 25, 2024 ▶ 9:30 The Secret Virtual Assistant Marketplace SaaS CEO's Spent $25m on in 2023
Disclosure
Singh: PAR Acquired Punchh for $500M Using Overvalued Stock
“We went out, we bought a half a billion dollar business called Punch, that's based here in Austin now, and we started using our stock because we thought it was very inflated, and so it was the greatest we ever did, because it built, it gave us tremendous scale…”
Savneet Singh Jul 23, 2024 ▶ 5:18 39 Year Old Public SaaS CEO Doubles Revenue to $400m Over the Last 24 Months - His Genius M&A Playbook
Disclosure
Lemlist turned down $20M and $30M investment offers to remain fully bootstrapped
“And then all of that, of course, attracted a lot of investors' attention, where we had a twenty million dollar investment proposal that we turned down before turning down a thirty million dollar investment, simply because we don't need the funds.”
Kevin Moenne-Loccoz Jun 18, 2024 ▶ 19:58 Lemlist Product Genius Shares Strategy, $23,000,000 in Sales (ARR), No Outside Funding
Disclosure
LMS365 rejected $50M term sheets with heavy secondary share sales
“We turned down a number of fifty million dollar term sheets with a lot of secondaries in there, but then it was like, hey, we don't want that valuation.”
Rasmus Holst Apr 16, 2024 ▶ 12:33 This Danish CEO Hit $30m ARR using Unique 14 Hub Model Selling Software for Microsoft Ecosystem
Disclosure
Dimitro Okunyev rejected a $10 million buyout offer from a public company
“Yeah, the offer was like quite nice. It was like, ten millions. I don't believe that this is the fair price so far.”
Dmitry Okunev Jan 23, 2024 ▶ 10:49 How to Make $3m Building a Slack Clone with no money, experience, or sales team
Disclosure
Inflectra pays zero sales commissions, favoring salaries and company-wide quotas
“We don't we don't carry individual quotas. We have a company quota and we, everyone's paid salary. We don't do any commissions. That's one unique feature.”
Adam Sandman Nov 14, 2023 ▶ 11:39 Founder Hits $13m Revenue with No VC Raised selling SaaS to Defense Firms
Disclosure
Adam Sandman owns 100% of Inflectra with no employee equity pool
“No, actually none. It's there's no I'm sole owner.”
Adam Sandman Nov 14, 2023 ▶ 14:32 Founder Hits $13m Revenue with No VC Raised selling SaaS to Defense Firms
Disclosure
Vidas shut down StrategyBox fearing ChatGPT would usurp its core tech
“We also saw we had early access to ChatGPT just because it was a data management platform, and we did AI and machine learning. I had a look at a lot of the functionality that we were building and investing in, and I looked at the capabilities of ChatGPT, and I…”
Aaron Vidas Nov 7, 2023 ▶ 4:46 How to do $500,000 Revenue in 8 Weeks launching new AI SaaS Tool
Disclosure
Gobel Received Tens of Millions in Zenerate Secondary Liquidity Payouts
“The payouts had been in tens of millions of dollars, right?”
Rab Gobel Nov 6, 2023 ▶ 14:39 Bootstrapper Reveals $7m Profits on $40m Revenue Selling to Banks, 2 Customers Pay $10m+ Each
Disclosure
Manageable's uncapped note has mandatory conversion at $300k raised
“We don't have a cap. We just have mandatory conversion which is if we, when we get to 300,000, then we have a mandatory conversion. Either 300,000 or December 31st 25 is our minimum... If I, if we raise 300,000 dollars, then that man, then that creates a conve…”
Steve Petersheim Oct 7, 2023 ▶ 6:37 Economics of a $37,500 Pre Seed Uncapped Convertible Note
Disclosure
Bhattacharya: 70% of Involve.ai's coding is generated by AI
“70% of our coding is now done with AI.”
Gaurav "G" Bhattacharya Aug 25, 2023 ▶ 16:03 Team of 12 Hits $2.5m in ARR, $64m Valuation for Customer Success Tool. Can they beat Gainsight?
Disclosure
Kumar self-funded $800k into Juggle before acquiring a single customer
“If I can say close to 800,000 dollars.”
Arun Kumar Aug 22, 2023 ▶ 9:25 Zero to $1m in 12 Months, how he used personal brand to scale SaaS Fast
Disclosure
Node.ai's initial ideal customer profile is MBA students
“Our initial ICP will be actually MBA students.”
Justin Shum Aug 11, 2023 ▶ 8:16 Can this new AI tool grow into their $10m valuation?
Disclosure
Node.ai is trying to disrupt Wikipedia
“We're trying to actually disrupt Platforms like Wikipedia.”
Justin Shum Aug 11, 2023 ▶ 16:00 Can this new AI tool grow into their $10m valuation?
Disclosure
A VC investor demanded an exit one year after funding Cleeng
“One of the investors, the one that came in actually in 18 we are facing a few challenges in in 19, and they tell us, look guys we'd like to do an exit at the time where we started to spend like crazy.”
Gilles Domartini Jul 27, 2023 ▶ 3:48 From (almost) bankruptcy to $20M ARR / $2M profit within 3 years
Disclosure
CB Insights has reached ~$100M ARR without a PR firm
“We're kind of in that hundred million ARR category, and we don't have a PR firm still”
Anand Sanwal Jul 21, 2023 ▶ 5:26 Don't do these 68 things in your SaaS company
Disclosure
Hurt: Data.world made zero revenue until 2018 after raising $50M
“At Data. World we didn't even make a dollar of revenue until we had raised over fifty million dollars. And we didn't break a dollar of revenue until 2018.”
Brett Hurt Jun 6, 2023 ▶ 16:17 How Investors Bought 50% of Data.World with 2.1m free users, accounts at 31k paid seats
Disclosure
Patel: NP Digital Acquired AnswerThePublic for $8.6M at $1M–$1.2M EBITDA
“Answer the public. We recently bought this company for 8.6 million, funny enough, from FE International that had a booth. And they were only doing one, 1.2 million in EBITDA, so we overpaid for it.”
Neil Patel May 17, 2023 ▶ 5:52 A New Way to Think About SaaS: How to Build a 9-Figure Company by Giving Software Away For Free
Disclosure
DealPad mandates executive sponsor access before conducting discovery or demos
“I won't let my team sell into a company. If we get past qualification, we do not sit discovery unless we get exec sponsor access. It's one of our conditions. If you want a demo, if you want to go through discovery with us, we need to have exec sponsors on that…”
Adam Baker Apr 24, 2023 ▶ 4:40 How to consistently win 7-figure software sales deals
Disclosure
SweetCX minority shareholders waived equity to boost founder payout in acquisition
“What we actually did, interestingly enough, is a couple of my shareholders said that they would waive their shares so that we could then pump those up a little bit. And the two founders who did most of the work, my CTO and myself, we get a little bit of a bump…”
Valerie Peck Apr 5, 2023 ▶ 8:38 Acquired! Why She Sold her Bootstrapped $800k ARR Company for $3m
Disclosure
QuestionPro demanded an asset deal for immediate year-one tax write-downs
“Because he wanted an asset deal, because he can write a hundred percent of the cost of the company down and immediately in year one.”
Valerie Peck Apr 5, 2023 ▶ 14:20 Acquired! Why She Sold her Bootstrapped $800k ARR Company for $3m
Disclosure
Berman: Always require upfront credit card details before offering SaaS trials
“I'm not a big fan of the free trial with no credit card. So the way that I always launch our SAS is Tapleo everything before is you get in there, you have to put in your credit card in order to see the SAS. And then there's a free trial after. So I go by numbe…”
Alex Berman Feb 24, 2023 ▶ 9:19 How to Clone Existing Company and Hit $10k MRR In Under 6 months
Disclosure
BoltCode founders have not discussed equity split prior to launch
“We really haven't discussed equity yet, because like I said, I'm getting most of the funding to the table, and most of the tech is mine. The other co-founder just handles operations, so we haven't really discussed it yet.”
Manonia KH Feb 23, 2023 ▶ 11:16 Should you negotiate co-founder equity first, or wait until you have customers?
Disclosure
Lempiäinen: GeekLab is raising at a $12M post-money valuation
“12, 12 to be exact.”
Jesse Lempiäinen Feb 20, 2023 ▶ 15:34 $720k in ARR SaaS Raising at $12m Valuation Right Now for App Install SaaS
Disclosure
Amit RG turned down Y Combinator after raising from Sequoia
“We also got selected by Combinator, but we decided to not go ahead with it. Because this thing happened like one week before YC, YC was all remote. I'm a big YC fan, but it didn't make sense, you know, to dilute so much when we were already getting, they wante…”
Amit RG Feb 15, 2023 ▶ 3:10 How he hit $2m ARR in 24 months for Ecommerce Support SaaaS, Raised at $20m valuation
Disclosure
Pang left QCC because his co-founders refused to raise capital
“Well, I want I wanted the company at least to raise another round of money to compete effectively, and it was profitable, and I made the we launched a very, very, very profitable advertising campaign across social media and Other media channels that, that actu…”
Zong Pang Jan 18, 2023 ▶ 15:37 He hit $100m Revenue, Built the Zoominfo of China, then quit last month. What happened?
Disclosure
Indicio's early angel investor attempted a takeover to become CEO
“But he had his own plan upon becoming the CEO of the company and Trying to push us into, to take more of his money and.”
Franz Andersen Jan 13, 2023 ▶ 13:14 How he bought out his $130k Seed Investor with $200k in new money, $7.5m valuation
Disclosure
JobPaths Measures Success by Training Engagement Rather Than Job Placements
“We are gauging our success rate mainly by the number of users that are taking our training classes or building resumes.”
Jack Fanus Dec 19, 2022 ▶ 8:53 How JobPaths Hit $1.2m in Revenue Helping Ex-Vets Get resources and jobs
Disclosure
Fanus Admits JobPaths Cannot Track Specific Job Placement Figures
“This is the problem with why I cannot answer that question, because each community has their own programs. They are running their own data. They're connecting with their own employers. They're just using my software. You're grading me as if I'm Indeed. I'm not…”
Jack Fanus Dec 19, 2022 ▶ 10:52 How JobPaths Hit $1.2m in Revenue Helping Ex-Vets Get resources and jobs
Disclosure
Earner prioritizes monthly active usage over net dollar retention
“We're not actively measuring all the dollar retention figures. Like we're focusing more on just kind of what we built so far. We're looking a lot more into monthly active users and what different features within our app our customers use.”
Enzo Ottens Dec 16, 2022 ▶ 8:10 SMB Tax App hits $20k MRR by getting 1k+ Signups and Converting 20-50% to $35/mo paid accounts
Disclosure
Zomentum's Series A valuation landed slightly below $100 million
“I'm slightly lower than that, but in that negotiation ballpark. Yes.”
Shruti Ghatge Dec 5, 2022 ▶ 11:29 She hit $250k MRR in November for Partnership SaaS, 4000 Customers, approx $90m Valuation
Disclosure
Kaevand refuses to raise outside funding for Instantly acquisitions
“I like these things like acquiring, like, different companies. It might be cool, like at some point, but I wouldn't raise money for it to do it. Maybe it's like a stupid business wise, but just for like our, Like the way we built this company and we like worki…”
Raul Kaevand Dec 2, 2022 ▶ 14:13 New SaaS goes 0 to $2.4m in 9 months using genius growth strategy
Disclosure
Dayton: Blind competing term sheet price drove a higher valuation and earnout
“And they didn't know all the terms. They just knew the price. Right. So, so they had much better terms and they bumped up the price and, you know, structured a two year earn out so that I could get all the money I wanted for the company.”
Adrian Dayton Dec 1, 2022 ▶ 4:44 How he sold his $2.3m SaaS with approx $500k EBITDA for $6m+ Cash
Disclosure
TypeStack employs an unusual ratio of five designers to four developers
“We have five designers for a four dev team.”
Silas Reddy Nov 23, 2022 ▶ 14:05 How this pre-revenue SaaS startup raised $1m last week at a $5m cap
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