From $0 to $165M: How Harsh Patel Built and Sold 3 Companies (and What He’d Do Differently)
Episode 3
Monday, February 17, 2025 • Duration 01:04:33
Harsh Patel is a repeat founder, investor, and board member who has built and sold multiple companies, including MakerSquare, Hack Reactor, and Galvanize, which had a $165 million exit. With experience scaling businesses from zero to one, finding product-market fit, and navigating M&A, Harsh has seen it all.
In this conversation, we discuss:
The hardest part of startup growth: Going from nothing to product-market fit
How Harsh hacked early distribution to get first customers
The rapid scale and exit of MakerSquare in under a year
What made Hack Reactor grow from $1M to $8M in revenue so quickly
How to know when to sell your startup
The future of crypto and AI, and why meme coins might be the next big thing
Why Harsh believes company equity will eventually live on the blockchain
And much more!
Brought to you by:
Fondo — The #1 accounting platform for startups. Get bookkeeping, taxes, and tax credits handled: TryFondo.com
From cold email to his 2 startups getting acquired for $100M+
Episode 2
Monday, January 27, 2025 • Duration 01:52:44
Brought to you by...
Fondo: Your all-in-one accounting platform for startups. Get your books closed, taxes filed, and cash back from the IRS. - https://www.tryfondo.com/
In this podcast episode, I had the pleasure of speaking with Chris Bakke, who shared his journey from working in private equity to finding success in the tech startup world. He described how his experience in private equity was challenging and often felt like a grind, which led him to seek a more fulfilling career in technology. This transition taught him the importance of hard work and resilience, especially when facing tough tasks that may seem unglamorous at first.
Chris emphasized that the key to his success was not just about having a great product but also about persistence and adaptability. He learned that building a business requires a lot of cold outreach and networking, which can be exhausting but ultimately rewarding. His insights highlight that maintaining mental health and motivation is crucial when navigating the ups and downs of entrepreneurship, as it can lead to significant achievements and personal growth
Timestamp (0:00) - Intro
(0:17) - Origin Story: Growing Up and Early Career
(0:48) - Transition from Private Equity to Tech Startups
(3:03) - Lessons from Private Equity: The Importance of Scrappiness
(8:21) - Building Interviewed: The Idea and Early Customers
(12:01) - Sales Process: From Cold Emails to Conferences
(35:05) - Acquisition by Indeed: The Negotiation Process and Insights
Host Links:
https://x.com/davj
https://www.linkedin.com/in/davjphillips/
Guest Links:
https://x.com/ChrisJBakke
https://www.linkedin.com/in/bakk3/
Trailer
Episode 1
Wednesday, January 15, 2025 • Duration 00:26
https://www.tryfondo.com/
🎧 START pod: Liam Karlsson & William Gyltman, Co-Founders of Rankad.ai "Turn AI visibility into revenue. On autopilot."
Episode 59
Tuesday, March 31, 2026 • Duration 12:05
Liam Karlsson had no clue why his SEO clients were losing traffic while rankings held
Then his 57-year-old mom asked ChatGPT for new running shoes
They already have the clicks The conversions The impressions The keyword history
What they do not have is a system that knows what to do with it.
So brands pay agencies $5,000 to $50,000 a month - and still lose money on ads
Matthew Chen built Laurence to change that.
A quantitative system for Amazon advertising. Built for continuous decision-making under profit constraints. Using existing ad copy, reinforcement learning, and custom models to run ads on autopilot.
When confidence is high, it acts When data is sparse, it borrows signal from similar keywords
The result: about 40% better performance for customers.
Amazon is the wedge. Autonomous performance marketing is the bigger vision.
00:23 What Laurence does 02:12 How the company found the wedge 02:47 The customer quote that changed the company 03:15 The flaw in the standard Amazon ad model 05:25 The move from Amazon to the wider internet 06:12 How Laurence uses transformers today
JJ Maxwell, CEO & Founder, Pillar (trypillar.com) "Your App's Copilot"
Episode 49
Tuesday, March 17, 2026 • Duration 16:37
Setting up a single trigger in Zendesk takes 30 clicks
With Pillar it takes one sentence
JJ Maxwell built an open source copilot you build into your app. Users talk to it in natural language and it drives the app for them
The problem: products can do a lot but users don't always know what's there. So they ask support. Or they churn
Before Pillar, JJ built a creator ad marketplace with about 40,000 creators. Then spent two years on another product through YC W24. About $30M on the platform, real users, decent growth.
Pivoted anyway.
As soon as he lost belief it was gonna work, he ripped the bandaid off
Web MCP is already rolling out. Companies trying to stop agents from taking actions are fighting a losing battle
🎙️ JJ Maxwell, Founder & CEO of Pillar (trypillar.com) on the Fondo START pod
01:56 What Pillar is: a copilot that’s easy to build into your app 02:19 Why users ask support or churn when product complexity hides value 03:05 “30 clicks” in Zendesk becomes a sentence 03:39 Why AI can do this now: models are better at reasoning and chaining actions 04:19 What implementation looks like: wrap existing frontend code and tool calls 05:25 Why teams can often get Pillar working in about a day 06:09 The Double journey, real traction, and the decision to pivot 11:00 Web MCP and why agent-ready software is coming 12:23 Why companies may not be able to stop agents from taking actions forever
Julian Weisser | The Solo Flippening: How 1-in-3 Startups Broke the Co-Founder Myth
Episode 36
Saturday, December 20, 2025 • Duration 18:18
The script has been the same for decades: find a co-founder
Investors demanded it. Accelerators screened for it.
The narrative became so entrenched that founders started pairing up out of obligation, not alignment.
Julian Weisser, founder of SOLO and ODF, has a name for this phenomenon: co-founders of convenience
And he's proving they're not just unnecessary-they're often the reason companies fail.
This week, Julian released 'The State of Solo Founding' report: "Today, solo founding is considered odd. Soon it will be the default. This report features exclusive Carta data alongside commentary from solo founders who have raised over $250M and the investors who backed them."
The comprehensive tracks solo founder rates across thousands of startups, the headline finding is historic: for the first time, over one-third of new startups are solo-founded (That's 36% in 2025, up from under 25% in 2019)
👉 Apply to the Solo Founders Program today. A three-month, in-person residency for 6 ambitious solo founders. Next cohort starts Jan. 23, 2026: solofounders.com/program
(00:44) Why the report matters now (02:17) The data: 24% → 36%, first year over 1-in-3 (04:32) 3 forces: AI, visible wins, collapsing narrative (06:00) Investor POV (07:30) Org design insight: cutting the middle layer (09:47) Download report: http://solofounders.com/report (11:01) ODF26: half the cohort flipped to solo (12:33) Inside SOLO (14:30) Why coworking doesn't work for startups(16:37) Outcomes: $1M ARR in 2 months & more(17:19) Follow @solofounding & @joinodf
Nate Matherson | Set It, Forget It—Scaling to 2,000+ Customers at Numeral
Episode 35
Friday, December 19, 2025 • Duration 15:05
Nate Matherson has spent 10+ years as a founder. He's built companies and even exited. After that first exit, he started angel investing in dozens of companies, then launched a fund.
Numeral was one of his early bets. He sent Numeral's CEO Sam an email. By the end of the day, he was working there as Head of Growth. Now he's helping scale the YC-backed sales tax platform serving over 2,000 customers.
Nate's seen what happens when founders don't think about sales tax. "They actually found out that they owed about a half million dollars in sales tax… the buyer subtracted that off what would have gone to the founders."
When Nate was a founder, he'd log into Stripe and that sales tax dashboard was lit up like a Christmas tree. Numeral does free nexus studies and monitoring — takes five minutes to set up, plugs into Stripe and Rippling, then runs itself.
They launched their SaaS product recently, and their whole concept is set it and forget it. They actually love it when customers don't log in. Some of Nate's new learnings? "When I was a founder, I was always pretty good at marketing. I was just marketing not-so-great products, which made marketing a lot harder." At Numeral, with the right product at the right time, everything clicked.
And he knows: great products make marketing easy. Timing makes it effortless.
Key Topics Covered
[00:10] $500K sales tax bill found during due diligence
[01:10] What is nexus and how it triggers
[01:51] From founder to angel to fund manager to operator
[04:02] 10+ years building, angel investments, vc fund
[05:27] Numeral: e-commerce to SaaS journey
[08:12] States that tax SaaS + global VAT complexity
[08:40] "Set it and forget it"
[10:37] Free nexus study + monitoring in 5 minutes
[11:24] What's working in growth
🎧 Startup Growth Podcast, Ep. 32 Jayden Clark | Moments to Flywheels: Founders Engineering Repeatable Reach
Episode 34
Thursday, December 18, 2025 • Duration 10:38
Jayden Clark didn’t abandon music. He re-scored it for distribution.
After music school, a hedge fund tour, and a B2B SaaS sprint, he launched MOTS—short, sharp episodes designed to be both of the moment and built to last a quarter.
His north star isn’t “go viral.” It’s “be clear.”
The insight is disarmingly pragmatic: structure is not the enemy of creativity—it’s the amplifier. Lists compress cognition.
A beginning–build–end gives every clip a runway and a landing.
When a five-replies-deep roast on X unexpectedly detonated, MOTS podcast already had the scaffolding to catch the surge. That’s the signature move: follow a consistent weekly cadence, then publish “emergency episodes” when the culture pops.
The result is a feed that feels alive without feeling random.
Key Topics Covered
Career path: SF Conservatory → hedge fund → B2B SaaS → MOTS + Atlas Media Labs
Jazz formulas = content formulas: two-five-one progressions, building blocks, beginning-middle-end
"Neither timely nor timeless": weekly SF tech culture + emergency current-thing episodes
Emergency episode #1: Brian Chesky's bench press
The viral ratio: Meta Ray-Bans clip → five-tweets-deep → Theo's reply → Seth's "roast" GIF
"16 hours of screen time": the competitive advantage
Distribution strategy across Twitter, YouTube, Apple, Spotify
Timestamps:
00:20) "neither timely nor timeless"
Sky Yang & Neo Lee | Content-Market Fit > Product-Market Fit: Why B2B Founders Are Getting Cloned
Episode 33
Tuesday, December 16, 2025 • Duration 12:44
Sky Yang (CEO) & Neo Lee (CTO) are Co-founders of Imagine AI, an AI-powered content engine that clones B2B founders—replicating their voice, context, and backstory to create scalable personal brands. Before Imagine AI, Sky was elected student body president at UCSD by 32,000 students at age 19, then secured $150 million in state funding for university housing through coalition-building and advocacy in DC, Sacramento and at the UC Board of Regents. He co-founded "Break the Outbreak," a nonprofit that delivered PPE across 18 states and 53 cities during COVID, earning commendations from Senator Dianne Feinstein and Congressman Eric Swalwell. Neo transferred from UCSD to Berkeley, then dropped out to build. He met Sky freshman year at a beach event—asking "Are you Skygodkingdom?"—before they went skydiving together and Neo cut Sky's hair in the woods after COVID.
Their catalyst was realizing founders were building in public on X but deals were happening on LinkedIn. After meeting advisor Gustaf, they pivoted distribution strategy to focus on where B2B founders actually live and transact. Sky calls this "content-market fit"—a state where your content hits your target customer every single time, creating scalable, repeatable inbound motion. They were fully booked from their first week post-YC launch, landing Series B customers. One founder messaged urgently, jumped on a 15-minute call, and paid on Stripe immediately. They recruited over Halloween weekend instead of partying. They hosted a yacht party with $10 billion in collective GDP (320 capacity, 750+ on waitlist). Neo's philosophy: "The product is just amplifying what we already are. Just be authentic." Sky's vision references Westworld: "Your agents will interact with each other instead of humans."
Key Topics Covered:
· What Imagine AI is: a chat-first AI clone with high-fidelity persona creation, subject matter expert interviews, and content engineering to hit content-market fit
· From X to LinkedIn: pivoting distribution to where B2B deals actually happen; Gustaf's advice on market selection
00:25 “We’re helping companies earn more money in AI search” 02:34 AI search is moving fast: new models, algorithms, protocols 03:05 A new source of income beyond Google traffic 03:31 AI search is growing fast, but has not outrun Google yet 05:34 Enter your domain and get inside the app in about 30 seconds 05:52 Visibility, competitor, and company data inside one platform 06:07 AI gives optimization tasks based on scan data 06:15 The agent executes tasks on your site 09:41 SEO rankings held, but traffic still disappeared 09:47 Liam’s mom used ChatGPT to buy running shoes 10:00 “That was like the seed of Rankad”
Where to find Julian Weisser: X: https://x.com/julianweisser LinkedIn: https://www.linkedin.com/in/julianweisser Website: https://weisser.io
Where to find SOLO: X: https://x.com/solofounding LinkedIn: https://www.linkedin.com/company/solo-founders Website: https://solofounders.com
Where to find ODF: X: https://x.com/joinodf LinkedIn: https://www.linkedin.com/company/solo-founders Website: https://joinodf.com
Newsletters: Texts with Founders: https://textswithfounders.com Multitudes: https://multitudes.weisser.io
Where to find David Phillips: X: https://x.com/davj LinkedIn: linkedin.com/in/davjphillips
Brought to you by: Fondo — All-in-one accounting for startups @ fondo.com
[13:28] Great products make marketing easy, timing makes it effortless
Brought to you by: Fondo — All-in-one accounting for startups: fondo.com
· Sky's origin arc: Chengdu → LA → Bay Area → UCSD student body president → $150M state funding advocacy → Break the Outbreak nonprofit
· Neo's journey: UCSD → Berkeley dropout → "Skygodkingdom" beach encounter → haircut in the woods → building startups pre-Imagine AI
· Content-market fit framework: when your content hits your customer every single time—scalable, repeatable motion with high-intent top-of-funnel inbound
· Week-one hypergrowth: fully booked post-YC launch, Series B customers, 15-minute Stripe close during conference, recruiting over Halloween
· Authenticity over algorithm: amplification not fabrication; the product shapes around you, not the other way around
· Building clones that replicate voice, context, backstory, heuristics, and cognition
· The $10B GDPyacht party: 320 founders, 3 DJs, 750 waitlist—building community as cultural moment
· The 'Westworld' thesis: AI agents interacting on your behalf
· Building in public as 2025 narrative: why founders do great work but nobody knows; solving discovery through personal brand at scale
· Design philosophy: one infinite content motion thread vs. scattered posts; AI handles artifacts, humans make strategic decisions
Chapters: 01:21 - The origin story: "Are you Skygodkingdom?" 02:00 - Neo cuts Sky's hair in the woods 02:36 - Sky's journey: Youngest student body president at UCSD 04:20 - Securing $150M in state funding for student housing 06:28 - The nonprofit during COVID 06:40 - How Imagine AI started: solving their own problem 07:15 - Launching on YC and getting booked solid 08:00 - Using their own product for personal branding 09:08 - What is "content-market fit"? 10:08 - The future: AI clones 11:09 - The $10 billion GDP yacht party in SF 12:11 - Where to find Sky, Neo, and Imagine AI
