Kevin was building a successful startup in the NFT space. They'd hit $1M ARR. But he looked at the market and realized it wasn't big enough. So he made the terrifying choice to pivot the entire company into cybersecurity.

In this episode, Kevin breaks down how he navigated that transition without killing the business. He reveals how he sold his first $5k/month contract with no product, why he raised a massive seed round he didn't need, and how he convinced Andreessen Horowitz to lead his Series A in the middle of a strategic shift.

Why You Should Listen

• How to pivot from a bad market to a unicorn opportunity.
• Why he sold a $5k/month contract with zero product.
• How to raise a Series A from a16z during a pivot.
• Why you never truly "find" Product Market Fit.
• The danger of building for a niche market (and how to escape).

Keywords

startup podcast, startup podcast for founders, product market fit, finding pmf, pivot, cybersecurity, crypto startup, a16z, raising series a, Kevin Tian

00:00:00 Intro
00:02:17 Meeting at Uber and the "Glass Eating" Phase
00:07:21 The First Idea
00:11:52 Selling the First $5k/Month Contract with No Product
00:16:52 The Decision to Pivot at $1M ARR
00:29:43 Network Selling to Enterprise Cybersecurity
00:32:03 Raising Series A from a16z During a Pivot
00:33:36 Why Product Market Fit is Not a One-Time Event
00:35:10 Action Produces Insights

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Dileep sold his first company for over $100M. For his second act, he didn't just want another win; he wanted to solve a problem that banks refused to touch: global business banking.

In this episode, Dileep breaks down how Jeeves scaled to $7M ARR in just over a year by doing things that "don't scale"—like physically mailing credit cards to Argentina.

He reveals the counterintuitive strategy of raising from dozens of small investors, how to pivot a fintech when interest rates skyrocket, and why being an outsider was his biggest advantage in building a global banking infrastructure from scratch.

Why You Should Listen

• How to get to $7M ARR in one year through unscalable acts.
• Why a "messy" cap table with 50+ investors is actually a secret weapon.
• The "Beat Down" Framework: A brutal stress test for vetting your idea.
• The offline marketing stunt that actually worked.

Keywords

startup podcast, startup podcast for founders, product market fit, fintech startup, global expansion, second time founder, Y Combinator, fundraising strategy, B2B banking, finding pmf

00:00:00 Intro
00:02:04 Selling His First Company for $100M
00:08:19 The "Beat Down" Framework for New Ideas
00:19:38 The One Metric That Matters for PMF
00:24:44 Why Join YC as a Second-Time Founder?
00:29:15 Shipping Cards to Argentina by Hand
00:39:13 The Pivot to Jeeves Pay When Cards Got Shut Down
00:43:25 The "Messy Cap Table" Fundraising Strategy
00:49:27 The Moment of True Product Market Fit

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Chaz has founded 3 companies. The first sold for over $40M. The second sold to GoPuff for even more. Now, he’s on his third act with Model ML, having just raised $75M Series A <2 years in.

In this episode, Chaz breaks down the playbook behind his successes. He reveals how he raised his first million by pitching strangers on LinkedIn, why his delivery startup was just a text message system on the backend, and why speed is the only defensive moat left.

Why You Should Listen

• How to pitch strangers on LinkedIn for angel checks.
• Why you should always say you're raising "a bit more" than you actually are.
• Why "Product Market Fit" is no longer static in the age of AI.
• How to launch a massive consumer business.
• Why getting a paid design partner isn't enough.

Keywords

startup podcast, startup podcast for founders, serial entrepreneur, fundraising strategy, product market fit, rapid scaling, AI startup, exit strategy, MVP, fintech

00:00:00 Intro
00:04:46 Pitching Strangers for Angel Checks
00:07:51 The "Fake" Fundraising Strategy
00:23:28 Why MVPs are Dead in the AI Era
00:25:01 Selling to GoPuff While Running Out of Cash
00:32:25 The Origin of ModelML
00:38:30 The Design Partner Playbook
00:46:13 From $5k to $100k MRR in 3 Months

Send me a message to let me know what you think!