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Every founder.Every PMF story.

301 conversations with founders building their next $100M+ company — the spreadsheets, the dead ends, and the exact moments PMF clicked.

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VCs chased crypto and passed on his “boring” startup—then he raised $385M at a $2B valuation. | Aaron Schumm, Founder & CEO of Vestwell

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Latest·Sep 7, 2026

VCs chased crypto and passed on his “boring” startup—then he raised $385M at a $2B valuation. | Aaron Schumm, Founder & CEO of Vestwell

Aaron started Vestwell in 2016. Two years in, he had $500K in ARR and an investor asking if it would ever make money. During the 2021 bull market, VCs told him 401ks were too boring—they were busy chasing crypto. Then Morgan Stanley signed. Today Vestwell has 2.5 million people saving on the platform, over $200M in ARR, and just raised $385M at a $2B valuation.In this episode, Aaron breaks down why he white-labeled everything instead of building his own brand, how losing the JP Morgan bid as a 40-person startup still turned into one of his largest partnerships, and how a methodical cap table let him raise a Series A on a couple hundred thousand in revenue.Why You Should ListenWhy letting your customers keep their brand beats competing with them.How to raise a Series A with only a few hundred thousand in ARR.Why losing an enterprise deal is the start of the sale, not the end.Why you never regret firing someone too soon.Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Vestwell, Aaron Schumm, fintech, 401k, retirement savings, enterprise sales, channel partnerships, white label software, Series A fundraising, Morgan StanleyChapters00:00:00 Intro00:02:05 The Morgan Stanley Deal That Proved PMF00:08:32 A 401k So Bad It Started a Company00:10:23 Building V1 in a Regulated Industry00:17:07 Turning Advisors Into a Sales Channel00:23:57 Raising an A on $200K of Revenue00:31:16 Too Boring for the Crypto Bull Market00:38:45 Losing JP Morgan, Then Winning It Back00:43:23 Never Regret Firing Too Soon

Every founder.Every PMF story.

VCs chased crypto and passed on his “boring” startup—then he raised $385M at a $2B valuation. | Aaron Schumm, Founder & CEO of Vestwell

He sold his 8-figure business to bet on a side app—then grew it to 20x in a year. | Andrew Antos, Co-Founder & CEO of Within

He spent $0 on marketing for 2 years—then raised $400M at a $3.25B valuation. | AJ Loiacono, Co-Founder & CEO of Judi Health

He spent $150K on brand before he had a product—then closed $1.5M ARR in 1 month. | Niklas Lindgren, Co-Founder & CEO of Endra

He lost all 5 of his first deals—then built the next Looker and raised $250M. | Colin Zima, Co-Founder of Omni

He fired almost everyone, kept 2 engineers—then grew 12x and raised a $30M Series A. | Rafael Broshi, Co-Founder of Notch

He worked out of a police department for free for a year—then built a $6.8B company. | Ben Rudolph, Co-Founder of Peregrine

1st-time solo founder does 90 interviews in 90 days—closes a $25M Series A 2 years in. | Damien Lewke, Founder of Nebulock

He tries 1,000 ideas a decade & kills nearly all—that's how X built Waymo & Google Brain. | Astro Teller, CEO of Moonshots at X (Alphabet)

He raised $75M—but kept his team to 21 people & pays everyone the same salary. | Cos Nicolaescu, Co-Founder of Accrual

He quit Stripe and hit $10M ARR in 4 years—with $0 marketing spend. | Anurag Goel, Founder of Render

He shut down his last startup and gave the money back—then hit $1M ARR in 6 months. | George, Founder of Monk

He quit his $50M ARR startup to work as a paralegal—then raised a $60M Series A. | Dan Mishin, Founder of Manifest

He churned 100% of his revenue on purpose—then grew 10x to $2M ARR in under 12 months. | Ali Khokhar, Founder of Amigo AI

He hit $1M ARR by sending 500,000 cold emails—then raised a $25M Series A in 6 days. | Mark Hughes, Co-Founder of Solidroad

Q1 2026 w/Carta: What you need to raise a Series A. | Peter Walker, Head of Insights at Carta

How to get a VC (like me) to wire you $2M in under 2 weeks (the FOMO playbook) | Solo Episode

Coinbase's ex-CPO bet on AI agents before ChatGPT—now he's closing 7-figure Fortune 500 deals. | Surojit Chatterjee, Founder of Ema

How this 1st-time founder went from closing customers for $500 a month to $300,000 a year. | Sean McCarthy, Founder & CEO of BackOps

He built for 2 years before raising a dollar—then hit $13M ARR and a $40M Series B. | Alex Halliday, Co-Founder & CEO of AirOps

180 VCs rejected him—then a $60K billboard got him to $2M ARR in 4 months. | Isaiah Granet, CEO of Bland AI

She bet on a consumer app when every VC wanted B2B—then grew to $10M ARR. | Anada Lakra, Founder of BoldVoice

He raised a $10M seed with no revenue—then grew 30x to $30M in year two. | Bobby Samuels, Founder of Protege

He ran Prime fulfillment for Amazon—then raised $20M to replace e-commerce with AI. | Maju Kuruvilla, Founder of Spangle

She got rejected by 22 VCs—then built 6sense to $100M+ in revenue. Now she's back for AI. | Amanda Kahlow, Founder of 1mind

How this AI founder is on track to hit $50M ARR just 2 years after launch. | Tarek Alaruri, Co-Founder of Stuut

He launched a free product for enterprise customers—then grew to $12M ARR in 2 years. | Bhaskar Sunkara, Founding CTO of AppDynamics

He raised $41M in one year to replace enterprise accountants with AI. | Yogi Goel, Founder of Maxima

How he grew his AI startup from $2M to $20M ARR in 12 months. | Omar Haroun, Co-Founder of Eudia

She raised $20M from Accel to replace QuickBooks with AI. | Helen Hastings, Founder of Quanta

He moved to the US with nothing. Now he does $750M ARR. | Mateo Marietti, Founder of CookUnity

This 3x founder hit $1M ARR in 5 months. Here's his playbook. | Roy Moussa, Founder of GetVocal

He made 0 sales for the first 8 months. Now he does $200M+ ARR. | Ryan Anderson, Founder of Filevine

He built heads down for a year. Then landed a $1M contract. | Sam Jones, Co-Founder of Method Security

He raised $150M with $0 revenue. Then hit $1M ARR in 4 months. | Michel Tricot, Co-Founder of Airbyte

He failed for 5 years. Then hit $20M ARR with 100% outbound. | Didi Gurfinkel, Founder of Datarails

His startup powers OpenAI's Voice Mode. Last month, they became a unicorn. | Russ d’Sa, Co-Founder of LiveKit

He pivoted at $1M ARR—then raised $120M. | Kevin Tian, Co-Founder of Doppel

He sold his first startup for $100M. Then raised $250M in 18 months. | Dileep Thazhmon, Founder of Jeeves

He sold his first 2 startups. His 3rd grew to $1M ARR in 3 months. | Chaz Englander, Founder of Model ML

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

He wrote the book on Account Based Marketing. Here are his GTM secrets for enterprise. | Bassem Hamdy, Founder of Briq

He got rejected from YC—then grew to $1.8B in under 2 years. | Max Junestrand, Founder of Legora

He sold dog food from his condo. Now he does $100M+ a year. | Russell Breuer, Founder of Spot & Tango

He made 100 cold calls a day. Now his startup is worth $600M. | Harman Narula, Founder of Canary Technologies

He got 100k signups in 30 days. They all churned. 2 years later, he hit $10M ARR. | Rich White, Founder of Fathom

He grew his startup to $150M ARR & an IPO. Now he's back for the AI wave. | Bob Tinker, Founder of MobileIron & BlueRock

How his AI-enabled Services startup hit $1M ARR in just 3 months. | Shahar Peled, Founder of Terra Security

He hit $1M ARR with just 2 people. 2 years later, he's worth $1.5B. | Ashwin Sreenivas, Co-Founder of Decagon

His 1st startup failed. His 2nd became a unicorn in just 18 months. | Jake Stauch, Founder of Serval

It took him 4 years to launch—then he hit $1M ARR in 30 days. | Siqi Chen, Founder of Runway

Solo Episode: B2B SaaS is dead. Here's what the best AI founders are doing instead.

He got rejected by 60 VCs, burned all his savings—then grew to $100M ARR & a $2B valuation. | Kyle Hanslovan, Founder of Huntress

He killed a $100K ARR product & pivoted—then raised $375M. | Viraj Parekh, Co-Founder of Astronomer

Solo Episode: The Five Steps to Product Market Fit

He killed a viral app with 50k users. 2 years later, he hit $10M ARR and raised $30M from Sequoia. | David Paffenholz (Juicebox)

Her VCs said she killed the company. 6 years later, it's worth $1.3B. | Jennifer Smith, Founder of Scribe

He exited to Snap for $166M— built an AI video startup, then raised $50M. | Alex Mashrabov, Founder of Higgsfield AI

How his AI-first services company grew $0 to $40M ARR in one year. | Eric Foster, Founder of Tenex

Q3 2025 w/Carta: What you need to raise a Series A. | Peter Walker, Head of Insights at Carta

He added AI to parking lots—then raised $3.5B. | Alex Israel, Founder of Metropolis

He left a $2B ARR company to build AI agents—then hit $1M ARR in < 6 months | Amit Shah, Founder of Instalily

He tested his idea in one weekend—then raised $120M. | Wayne Slavin, Founder of Sure

At 21 he made his 1st million. At 23, he grew his startup to $8M ARR in 6 months. | Matt Espinoza, Founder of Clover

He walked away from $5M ARR—then built a $50M company. | Russ Fradin, Founder of Larridin

He made 2 key changes —then grew to $100M ARR in 2 years & exited for $2B. | Harish Abbott, Founder of Deliverr & Augment

He built a $20B public company, left—then raised a $100M Series A. | Dheeraj Pandey, Founder of Nutanix & DevRev

He built a new database in his bedroom—now he powers Cursor, Notion and Anthropic. | Simon Eskildsen, Founder of turbopuffer

He burned $4M to hit $100K ARR—but with 1 big change, he grew to $4.5M ARR in just 12 months. | Guy Podjarny, Founder of Snyk & Tessl

5x founder asked Ford for a contract so large—they acquired his company instead. | Amar Varma, Founder of Mantle

He "kind of" had PMF for 8 years—until, after a rebuild, he raised $100M | Ben Alarie, Founder of Blue J

They failed every POC—then grew their cybersecurity platform to $100M ARR in 5 years. | Dean Sysman, co-founder of Axonius

He tested his pitch on Uber drivers—then built a cybersecurity platform to $180M raised. | Casey Ellis, Founder of Bugcrowd

He quit Google & his 1st startup failed—but his 2nd grows at $1M ARR every 10 days. | Zach Llyod, Founder of Warp.dev

He tried to return $200K to investors 30 days in—then exited to Microsoft 5 years later. | Alex Sherman, Founder of Bluefish AI

A drug dealer threatened to kill him—then he grew 50x in 3 Years to $50M ARR. | Brett Carlson, Found of ServiceUp

He pitched 100 VC and spent 3 years building— then grew to $7B AUM. | Doug Scott, Founder of Ethic

PMF Observations: Speed is the only startup moat—& why most founders lose it.

He spent 5 months working with customers before building—then grew to $10s of millions ARR. | Aviv Leibovici, co-founder of Buildots

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