The Ledger

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Disclosure
Cheek built an early database using discarded business cards found on streets.
“I'm probably going to get sued for saying this, but I used to pick up business cards off the street in New York city and add them to my database.”
Lori Cheek Dec 2, 2020 ▶ 13:53 The Truth About Patents: 'I Did Everything Right — It Hurt Me'
Disclosure
Marketers can connect Ahrefs to Claude to reverse-engineer AI search citations
“So one of the things, for instance, that I use is we've got, ah, Ahrefs for SEO and AI tracking, and I've connected that to Claude And I'll have Claude, again, it's great at analyzing data. I'll have it go in there and analyze all of the tools. There's multipl…”
Clayton Critchard Sep 8, 2026 ▶ 26:32 Getting Laid Off Led Him to Buy the Company That Hired Him
Disclosure
Heights Platform AI detects customer frustration to trigger human escalations
“And if our AI detects that, hey, maybe this person's a little bit frustrated, even if they didn't ask to talk to a human, it'll escalate it to us.”
Brian McCanulty Sep 1, 2026 ▶ 32:16 Nobody Wakes Up Excited to Use Software - So He Built This Instead
Disclosure
Weisbrot: Three strategic criteria required before implementing new software features
“I'm trying to look at it from the point of view of if I'm going to implement this, how does it either make it more sticky, make it more obvious to say yes to in the beginning or make the learning loop more intelligent. And if it could do one of those three thi…”
Sean Weisbrot Aug 25, 2026 ▶ 23:25 Would You Rather Be a CEO or COO?
Disclosure
Todd Anthony: Pinwheel Agency is a $3 million time-and-materials business
“For an agency owner that is doing work, time and materials, and trying to maintain a, you know, a three million dollar business it's challenging”
Todd Anthony Aug 11, 2026 ▶ 1:49 AI Is a Block of Clay and Most Founders Never Sculpt It
Disclosure
Snyder: Claude Enterprise Cut Data Analysis Time From Weeks to Days
“We do use AI now, so we have a enterprise account through Claude, through Anthropic, and that has significantly sped it up. I mean, that was about two weeks of manual data formatting and crunching to accomplish the analysis five years ago, and today that the f…”
Dustin Snyder Aug 4, 2026 ▶ 18:34 Talking to the $25/hr Shop Floor Worker Beat Every Spreadsheet
Disclosure
Gurovich: Voice AI Addresses Accessibility for Elderly Users with Vision Loss
“My strategic bet is on voice.ai, because It's not just easier for non-digitalized people, but for example, when you get, you're getting old, you're starting to have some problems with your eyes, for example, yeah and other kind of stuff, and actually hear voic…”
Igor Gurovich Jul 28, 2026 ▶ 6:35 His Grandpa Worked Until 90 and Changed How He Sees Aging
Disclosure
Weisbrot: Chooses deterministic automations over AI agents due to lack of trust
“I've implemented dozens of automations into my podcast operations. And I did it as automations, not as agents, even though everyone on the internet is trying to sell me agents. I did it because I don't trust agents. At least not yet.”
Sean Weisbrot Jul 21, 2026 ▶ 12:14 80% of the Workload Done Before a Human Touches It
Disclosure
Narasin passed on 2,500 startup pitches and funded only one last year
“Last year I passed on 2500 pitches. I only funded one.”
Ben Narasin Jul 14, 2026 ▶ 0:32 Happiness Found Him Through a Crappy Movie at 2AM
Disclosure
Goyal: LinkedIn is the single largest source of his career success and pipeline
“LinkedIn has been the single largest source for all of my career successes, I would argue, but definitely the source of pipeline, definitely the source of building trust and building relationships, right?”
Neal Goyal Jun 30, 2026 ▶ 1:40 1 Out of 100 Sellers Does This. He Built 8x Pipeline Doing It.
Disclosure
Goyal vows never to use AI-generated direct messages for sales outreach
“AIDMs never in a million years would I ever engage in such.”
Neal Goyal Jun 30, 2026 ▶ 20:33 1 Out of 100 Sellers Does This. He Built 8x Pipeline Doing It.
Disclosure
Shelton Mercer: Meeting with U.S. World Cup Host City Leaders on Permanent Investment
“I mean, right now we've been meeting with leaders in America around the, that have host the world cup cities where the world cup is being hosted this summer and the ideas to have some permanence.”
Shelton Mercer Jun 23, 2026 ▶ 2:01 60 Days Down to 60 Minutes Changed How Shelton Thinks About His Own Team
Disclosure
Indries: Due diligence framework utilizes nearly 170 total questions
“We have a standard of 21 questions, and, you know, we analyze stuff, and wherever we feel that something isn't adding up, we go deeper, and then we go deeper. Just, you know, for the sake of the audience, we have almost a 170 questions total, you know, that we…”
Robert Indries Jun 16, 2026 ▶ 1:23 He Built LLMs in 2016 and Still Trusts Gut Over AI
Disclosure
McGregor: Building safe calling prototype in GSMA Foundry with Google and Ericsson
“We're gonna build a prototype for the world to look at, to test, and the rest of it is live. And I've invited Google And Ericsson, so California, Sweden, to join me in, in the foundry. And the first endeavor is to create, and I'll call it into six G, but now f…”
Travis McGregor Jun 9, 2026 ▶ 26:07 He Presented from the Hip on Stage and Invented a World First in 90 Days
Disclosure
Weisbrot lost over $500,000 of his personal funds in a startup failure
“And if I had known before that it's not what I wanted, then I would have saved myself years of suffering and over half a million of dollars lost or that I had invested that of my own money that, you know, I'll never recover.”
Sean Weisbrot Apr 21, 2026 ▶ 10:37 30 Years Exposed Him to Every Networking Context - His Conclusion Surprised Me
Disclosure
Sean Weisbrot: Living in China for Ten Years Muted His Outward Emotions
“I was a 10 years in China. And in inside mainland China, like people don't really show their emotions too much. So over 10 years of living there, I kind of stopped really showing my emotions, even though I didn't stop feeling them.”
Sean Weisbrot Apr 14, 2026 ▶ 9:43 What Matters Most and How Much Is Enough
Disclosure
Weisbrot: Skipping Extensive Guest Research Preserves Curiosity for Podcast Interviews
“I don't prepare anything other than the intro call. Right? So I'll do a little bit of research on them before I decide if I want to do an intro call. But I know there's some people that they'll spend hours doing tons of research just so they could have the per…”
Sean Weisbrot Mar 24, 2026 ▶ 8:17 Your Guests Are Getting Famous From Your Show And You Are Not
Disclosure
Alumni Ventures caps pre-Series A checks at $300k–$500k including syndication
“We're frequently around 50 or a hundred K. If we really have very high conviction on something, maybe it's a late seed or, you know, the syndicate is just phenomenal and there are other indicators of really rapid growth. We might also syndicate it in addition …”
Ron Levin Mar 17, 2026 ▶ 26:12 Why the Co-Founder Who Stayed CEO Was the Right Call
Disclosure
Alumni Ventures writes follow-on checks up to $8M–$10M in later rounds
“And later we do write million up to call it eight or ten million depending on many factors.”
Ron Levin Mar 17, 2026 ▶ 26:38 Why the Co-Founder Who Stayed CEO Was the Right Call
Disclosure
Wong will invest $10,000 in startups building systems using OpenClaw
“I'm going to start a program for anybody who use OpenClaw to, we want people to build startups from using OpenClaw, and we'll put a little bit of money, we'll put 10 K into, I mean, I don't want to say winning team because there is a potential we do more than …”
Sze Wong Mar 3, 2026 ▶ 19:35 OpenClaw is the Most Dangerous AI Tool Ever Built
Disclosure
EightX deploys AI agents to monitor client calls and sentiment
“So we have like a client coordinator agent who's listening to all the calls, taking notes, giving notes to our internal teams. . And also like listening for sentiment.”
Matt Putra Feb 3, 2026 ▶ 2:00 Profitability Is Not a Math Problem, It Is a Human Problem
Disclosure
Putra seeks quick startup exit to hedge against AI disruption
“I think my approach is to try to create a valuable company very quickly exit so that my family's okay. And yet still choose to believe in the utopia, even though I'm maybe buffing the downside.”
Matt Putra Feb 3, 2026 ▶ 23:03 Profitability Is Not a Math Problem, It Is a Human Problem
Disclosure
Weisbrot: Claude in Cursor generated full SaaS architecture and spec documents
“I used Claude inside of Cursor to create all of my documents. It created the roadmap. It created the feature specifications. It created the user stories. It created the technical architecture documents. It created all that stuff that like years ago when I had …”
Sean Weisbrot Jan 20, 2026 ▶ 12:56 He Let Go of 50 People After One Tool Changed Everything
Disclosure
Sadan: Duda Has Not Spent One Dollar Acquiring SMBs Since Agency Pivot
“From that day onwards, we didn't spend a dollar until today to acquire a small business.”
Itai Sadan Jan 6, 2026 ▶ 24:16 65% of Their Sites Now Start This Way (Most Founders Miss It)
Disclosure
Sean Weisbrot: Invested over $500,000 of personal consulting profits into tech startup
“I had an eight figure consulting business and I personally walked away with a lot of that money and I started a tech company and I put in over half a million of my own money to that business before I raised any money from other investors.”
Sean Weisbrot Dec 12, 2025 ▶ 15:01 Why You Should Stop Fundraising and Triple Your Prices (Coaching Session)
Disclosure
Weisbrot: Abandoned Vibe-Coded SaaS Startup After Breaking API Integration
“And it was working. I got everything working. It was perfectly good. I was ready to get those companies on, and then I had made an update, and it broke the API relationship. And I spent weeks trying to fix it, and I couldn't, and I said, I'm just gonna give th…”
Sean Weisbrot Dec 9, 2025 ▶ 24:02 We're Forced to Automate or Get Left in the Dust
Disclosure
Windley's recruiting business lost 75% of revenue at COVID-19 onset
“We dropped. 75% of the business. I put people on furlough, which was ended up being a good move instead of laying them off completely.”
David Windley Nov 25, 2025 ▶ 2:06 He Built a Mutual Fund Out of 200 Recruiting Clients and Hit $50M
Disclosure
Ustinov: My Company Manages $100M Per Year in Digital Ad Spend
“Actually we manage one hundred million dollars per year in ad spend”
Seva Ustinov Nov 18, 2025 ▶ 9:04 He Manages $100M in Ad Spend With a Trick Nobody Tried Yet
Disclosure
Lazerow: Velvet Sea Ventures manages about $400M in AUM
“We have a VC business, which, you know, about four hundred million assets under management, Velvet Sea Ventures.”
Michael Lazerow Nov 11, 2025 ▶ 2:10 Sold for Nearly $1B and Spent 3 Years Lost in a Painting Studio
Disclosure
Lazerow details backing Scopely at the seed stage before its $5B exit
“The five billion dollar exit. That's scopely one of our seed investments had to Savvy Games.”
Michael Lazerow Nov 11, 2025 ▶ 6:06 Sold for Nearly $1B and Spent 3 Years Lost in a Painting Studio
Disclosure
Lazerow backed Liquid Death pre-launch without knowing it would reach $1B
“Liquid Death is a really great example of here's a creative director, Mike Cesario, who comes up with an idea to market a wellness product, water, in a very novel, innovative way across social media. Did we think it was going to be a billion dollar plus compan…”
Michael Lazerow Nov 11, 2025 ▶ 6:27 Sold for Nearly $1B and Spent 3 Years Lost in a Painting Studio
Disclosure
Lazerow: Liquid Death is his only CPG investment
“I don't invest in the food space often. You know, Liquid Death is the only CPG company, but I love the space.”
Michael Lazerow Nov 11, 2025 ▶ 37:19 Sold for Nearly $1B and Spent 3 Years Lost in a Painting Studio
Disclosure
Lulo: Alleyoop produces 250 LinkedIn content pieces monthly from employees
“And right now we're producing 250 videos and pieces of content on LinkedIn a month from just my employees.”
Gabe Lulo Oct 17, 2025 ▶ 24:55 Connect With People Liking Your Competitors' Posts Every Day
Disclosure
Bhargava: NB Group raises capital deal-by-deal instead of using a fund
“So our model is that we raise Capital specific to each deal. So when we make an investment, we have institutions that we work with who will back that specific deal. We don't have a fund that we drawn for every investment.”
Neel Bhargava Oct 7, 2025 ▶ 2:21 Why Two of Neel's Best Deals Came From Knowing an Industry Too Well
Disclosure
Blue: Saltbox Is Transforming Into an AI-Native Services Firm
“We're spending a lot of time making sure that we're transforming ourselves into a, an AI enabled services organization, not a services organization that sometimes uses AI.”
David Blue Sep 23, 2025 ▶ 19:00 Why B2B Companies Moving Reps Off Repeat Orders Are Winning
Disclosure
Kwan: Four15 Digital's Mexico Team Was Unaccustomed to Direct Leadership Feedback
“Even in our office in Mexico, it's a different culture in the way they do business. They are not accustomed, at least their, at least the team, I can't speak for everybody in Mexico. Maybe there are companies that have a different sort of way of doing business…”
Borja Kwan Aug 19, 2025 ▶ 14:39 He Fell on His Sword in Front of 20 Employees and It Worked
Disclosure
Weisbrot Uses Gemini to Replace a 5-to-10 Person Advisory Team
“A point for me to start from is that I currently use Gemini for a lot of things. Like it's my chief marketing officer, my chief product officer, my chief revenue officer, my chief customer success officer. It, it's constantly giving me advice on different situ…”
Sean Weisbrot Jul 29, 2025 ▶ 9:37 Europe Is Half as Likely to Adopt AI. Here Is What That Costs Them
Disclosure
McKay: Order Editing is built intentionally for an acquisition
“We have the ambition of wanting to get acquired. That's always been the vision for this company is we're building a medium sized business.”
Hamish McKay Jul 18, 2025 ▶ 4:17 Why Every Checkout Will Have This in 5 Years
Disclosure
McKay: 60% to 70% of Order Editing's software is built with AI
“Now somewhere between like 60 to 70% of our software is probably built with AI or in copilot with AI.”
Hamish McKay Jul 18, 2025 ▶ 15:02 Why Every Checkout Will Have This in 5 Years
Disclosure
Weisbrot vows never to raise venture capital or private equity again
“It's not something I want to be involved in anymore. I did it once and didn't see the success I thought I would see, and I learned my lesson from that.”
Sean Weisbrot Jun 24, 2025 ▶ 10:12 She Uses BITES Monthly and Her Clients Never Fear a Bad Quarter
Disclosure
Sean Weisbrot Rejected a $30,000 Offer to License Podcast for AI Training
“So I had someone come to me wanting to license my content for the purpose of tossing it into an AI and training it. And what I didn't know at the time, I told them, no, I said, I looked at the contract. I said, this doesn't look right for me. You're telling me…”
Sean Weisbrot Jun 20, 2025 ▶ 3:04 Licensing Revenue Dropped Tenfold in 15 Years. Now What?
Disclosure
Davis: People First automatically removes creators posting offensive memes
“We're automatically getting rid of any accounts that would have, you know, any racist or sexist or homophobic memes, all that stuff just gets kind of automatically pulled out of the database. Cause we're ingesting like all publicly available information across…”
Ryan Davis Jun 17, 2025 ▶ 9:00 Stanford Found More Brand Notes Made the Content Perform Worse
Disclosure
Weisbrot: I will never raise from outside investors again
“I will never raise from investors again.”
Sean Weisbrot Jun 6, 2025 ▶ 20:04 Self-Confidence Is a Terrible Substitution for Self-Awareness
Disclosure
Adam Shell lost millions in a failed California cannabis industry venture
“I face plan in the cannabis industry really badly. I lost millions of dollars. I'm still bereft with, I lost my money. I hurt my wife, my children. I lost investors' money, farms, farmers, like dude, it was Netflix bad.”
Adam Shell Jun 3, 2025 ▶ 22:17 One Turns the Lights On. The Other Walks You Toward Them.
Disclosure
Nanavati: Cimphony has built 40 to 50 specialized AI legal agents
“What we've done is we've built about 40 to 50 agents that are highly specialized for their particular use case within their particular work call.”
Arpan Nanavati May 30, 2025 ▶ 15:26 Why Founders Stopped Being the Human in the Loop
Disclosure
Yahes: Staffing agency paid ads generate high clicks but zero calls
“In this case, my, I've advertised a ton. The click through rates are very good, but the book a call rate is non-existent.”
Matthew Yaes May 23, 2025 ▶ 12:48 He Let a Filipino Team Run His 7-Figure Agency for 2.5 Years
Disclosure
Struppelhoff: Red Hawk Uses Google Gemini to Draft Project Backlogs
“For example, if a client gives me a what they would might consider a fairly detailed spec, I'm thinking about creating X. I'll submit that in through Gemini through our paid account so that it's all, you know, compartmentalized. It's not going out there into t…”
Matt Struppelhoff Apr 22, 2025 ▶ 18:54 AI Can Write Code, But It Can't Do Architecture
Disclosure
Bishop: A Single Vendor Dependency Killed a Profitable Business Sale
“We eventually weren't able to get a buyer for that business for that very reason, because of that singular dependency. That one vendor.”
Cameron Bishop Apr 8, 2025 ▶ 27:12 It Was Printing Money But Every Buyer Walked Away
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