A Product Market Fit Show | Startup Podcast for Founders
Pablo Srugo
59 episodes
He had paying customers before he even incorporated—then hit $1M ARR in a year and raised a $19M Series A. | Rahul Shivkumar, Co-Founder of Assured
- Assured raises a $19m Series A led by Insight in July for AI agents that automate provider credentialing and payer enrollment.
- Assured rejects AI BDRs for six human BDRs making 150-200 calls a day, citing healthcare pickup rates near 8%, roughly 4x other industries.
2 Nov · 57 min
His free app hit 200 locations and nobody used it, then he raised $25M. | Tushar Mishra, Co-Founder & CEO of Delightree
- Delightree raises a $25m round from Excel, bringing its total funding to about $50m after years of missteps.
- Tushar Mishra says Delightree's free app failed because free users had no commitment and few actually used it, so the company restructured around paid pilots.
26 Oct · 49 min
Carriers wouldn't talk to him, so he started with kids' smartwatches—then landed AT&T, Revolut and Klarna and now wins 90% of deals. | Hermann Frank, Co-Founder & CEO of Gigs
- Hermann Frank says Gigs found product-market fit in kids smartwatches, then fintechs like Nubank, Revolut and Klarna, and now wins over 90 percent of deals.
- Frank argues product-market fit is a gradient, and founders usually believe they have reached it far earlier than they have.
19 Oct · 46 min
He has cold outbound data on 40 million startups. Here's what works. | Daniel Saks, Co-Founder of Landbase and AppDirect
- Landbase's benchmarking, to be presented at Pavilion in September, shows more than 2x the precision of Apollo, ZoomInfo and Clay.
- AppDirect generates upwards of $10bn in gross merchandise value and owns brands including PartnerStack and FirstBase.
12 Oct · 54 min
He introduced his buyers to VCs instead of pitching them—then closed 20 deals in a row and a $20M Series A | Jonathan Awad, Co-Founder & CEO of Baselayer
- Baselayer closed 20 deals in a row with no losses, which CEO Jonathan Awad calls product-market fit.
- Awad's hack: introduce buyers to VCs instead of pitching, which he says worked all 40 times.
5 Oct · 1 h 2 min
He runs 3 dinners a week instead of cold outbound—and closes $500K+ ARR deals. | Nick Fleisher, Co-Founder & CEO of Sandstone
- Sandstone raises a $30m Series A for AI software that manages in-house legal work and context.
- CEO Nick Fleisher runs two to three dinners a week that almost always convert prospects to a first demo.
28 Sept · 49 min
Revenue fell from $25M to $8M—so he raised $75M in crowdfunding and ignored VCs. | Dan Novaes, Co-Founder & CEO of Mode Mobile
- Mode Mobile's revenue fell from $25M in 2022 to $8M in 2023, forcing half its staff cut.
- CEO Dan Novaes raised $5M via Reg CF and $75M via Reg A crowdfunding, mostly from retail investors over 55.
21 Sept · 51 min
He turned off a product with 20M users and went from 70 people to 7—then raised a $47M Series A. | Keith Peiris, Co-Founder & CEO of Lightfield
- Keith Peiris shut down Tome, a 20M-user product, cut 70 staff to 7, then raised a $47M Series A for Lightfield.
- Tome's low customer acquisition cost came with high inference costs and roughly 20% net dollar retention, making it dispensable.
14 Sept · 46 min
VCs chased crypto and passed on his “boring” startup—then he raised $385M at a $2B valuation. | Aaron Schumm, Founder & CEO of Vestwell
- Vestwell raises $385M at a $2B valuation on over $200M ARR from its "boring" 401(k) business.
- Vestwell finds product market fit in 2020-2021 when Morgan Stanley signs on as a core component of Morgan Stanley at Work.
7 Sept · 50 min
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
- Within sold its $10M finance business and grew its new product to nearly $20M in 18 months.
- The company found product-market fit three times, most recently with a tool splitting work between people and agents.
31 Aug · 50 min
He spent $0 on marketing for 2 years—then raised $400M at a $3.25B valuation. | AJ Loiacono, Co-Founder & CEO of Judi Health
- Judi Health's defining moment came about two years in, when a Fortune 500 company that read AJ Loiacono's post contacted it directly to buy its service.
- Loiacono argues that pharmacy benefit managers owning pharmacies and rebate businesses have a conflict of interest, since they earn more when drug prices rise.
24 Aug · 55 min
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
- Endra closes $1.5m in enterprise revenue in January 2026 at roughly $300,000 average contract value.
- Endra, which bundles legacy MEP tools like Revit into one AI platform, raises a $50m Series A in June.
17 Aug · 46 min
He lost all 5 of his first deals—then built the next Looker and raised $250M. | Colin Zima, Co-Founder of Omni
- Omni loses all five deals from unaffiliated customers who had verbally committed before finding product-market fit in mid-2023.
- Omni raises over $250m and effectively starts with $30m, funding product investment before revenue.
10 Aug · 53 min
He fired almost everyone, kept 2 engineers—then grew 12x and raised a $30M Series A. | Rafael Broshi, Co-Founder of Notch
- Notch raised a $30M Series A from Headline after firing almost everyone and keeping one or two engineers.
- Rafael Broshi marks product-market fit at a late-entry POC that became a four-year, ~$1M-a-year contract with a large insurance carrier.
3 Aug · 53 min
He worked out of a police department for free for a year—then built a $6.8B company. | Ben Rudolph, Co-Founder of Peregrine
- Peregrine raises a $250m round at a $6.8bn valuation, eight years after Ben Rudolph co-founded it.
- Peregrine started by working free inside the San Pablo Police Department for over a year, helping detectives solve a gang homicide.
27 Jul · 41 min
1st-time solo founder does 90 interviews in 90 days—closes a $25M Series A 2 years in. | Damien Lewke, Founder of Nebulock
- Nebulock raises a $25M Series A two years in, after $8.5M from Decibel and Bain Capital Ventures.
- Damien Lewke does 90 customer interviews in 90 days, altering Nebulock's architecture and killing a planned system.
20 Jul · 50 min
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)
- Astro Teller's X tries 1,000 to 1,500 ideas a decade, killing nearly all, to produce a couple of Google Brains, Waymos, or Wings.
- X funds projects for five weeks or five months rather than five years, and teams must write kill criteria or the default is to kill.
13 Jul · 48 min
He raised $75M—but kept his team to 21 people & pays everyone the same salary. | Cos Nicolaescu, Co-Founder of Accrual
- Accrual co-founder Cos Nicolaescu says the company's first real product-market fit signal came about a year in, when complex-document returns from firms like Armanino and Creative Planning showed staggering savings.
- Nicolaescu says customers asking for adjacent tax returns and audit-side use is the real validation, and Accrual's pilot-to-production conversion rate is 100%.
6 Jul · 58 min
He quit Stripe and hit $10M ARR in 4 years—with $0 marketing spend. | Anurag Goel, Founder of Render
- Anurag Goel says Render's word-of-mouth growth came from application developers, who love trying new tools and telling others about them.
- Goel says Render's fast time to value, where a connected GitHub repo spins up a live server with a URL and certificates, sets it apart from AWS.
29 Jun · 48 min
He shut down his last startup and gave the money back—then hit $1M ARR in 6 months. | George, Founder of Monk
- George says Monk, an AI accounts receivable automation company, reached $1m in ARR roughly six months after it started selling.
- George says he returned the money from Gattaca, his profitable computer vision startup, because the market was small and after a cofounder breakup.
22 Jun · 46 min
He quit his $50M ARR startup to work as a paralegal—then raised a $60M Series A. | Dan Mishin, Founder of Manifest
- Dan Mishin quits his $50M ARR real estate startup to work as a paralegal, then raises a $60M Series A for Manifest OS.
- Manifest OS recruits experienced lawyers, gives them a centralized back office with an AI-native paralegal, and rejects selling efficiency software to hourly-billing firms.
15 Jun · 43 min
He churned 100% of his revenue on purpose—then grew 10x to $2M ARR in under 12 months. | Ali Khokhar, Founder of Amigo AI
- Amigo AI churned nearly all its existing customers, refunded them, and pivoted to healthcare enterprise after a 240 thousand dollar deal exposed the mismatch.
- Ali Khokhar says revenue crossed its previous high within two months of the pivot, then grew five to ten times that level.
8 Jun · 53 min
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
- Solidroad reached $1M ARR mainly through cold outbound, sending about 500,000 emails through Lemlist that produced 40 customers at roughly a $25k ACV.
- Solidroad pivoted from sales role play to customer support after startups did not have the problem and larger support organizations used the tool more.
1 Jun · 43 min
Q1 2026 w/Carta: What you need to raise a Series A. | Peter Walker, Head of Insights at Carta
- Peter Walker says the typical Series A has grown from about $8 to $10m to $13 to $15m, and he would be most cautious investing there now.
- Walker says the Series A bar is about twice what it was, with founders now needing a $500m to $1bn story and about $3.5m in ARR.
25 May · 38 min
How to get a VC (like me) to wire you $2M in under 2 weeks (the FOMO playbook) | Solo Episode
- Pablo Srugo, a partner at Mistral, says fundraising is 80% the business and 20% process, and his playbook targets the controllable 20%.
- Srugo's math says three term sheets need about 50 outreach names, 40 first meetings, and 10 partner reviews, so founders should build that list before outreach.
18 May · 22 min
Coinbase's ex-CPO bet on AI agents before ChatGPT—now he's closing 7-figure Fortune 500 deals. | Surojit Chatterjee, Founder of Ema
- Surojit Chatterjee, founder of Ema, says he knows product-market fit has arrived when his average salesperson can close deals without him in the room.
- Ema's breakthrough came with Hitachi, where deploying to production HR data, not signing the contract, was the milestone that counted.
11 May · 37 min
How this 1st-time founder went from closing customers for $500 a month to $300,000 a year. | Sean McCarthy, Founder & CEO of BackOps
- BackOps won two enterprise deals against a well-known AI company after Sean McCarthy gave it a 5% chance.
- BackOps raised a $6m seed, twice the median, with six or seven term sheets, choosing Construct.
4 May · 56 min
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
- AirOps raised a $40M Series B from Greylock and reached $13M ARR in Q4 2025.
- CEO Alex Halliday built AirOps nights and weekends for almost two years before raising at the end of 2022.
27 Apr · 41 min
180 VCs rejected him—then a $60K billboard got him to $2M ARR in 4 months. | Isaiah Granet, CEO of Bland AI
- Bland AI replaces a typhoon-hit enterprise call center, resolving calls at a higher rate than human agents.
- Bland AI fires 50% of customers after its Series A, dropping below $1M to shed white labelers and resellers.
20 Apr · 52 min
He sold his first 2 startups. His 3rd grew to $1M ARR in 3 months. | Chaz Englander, Founder of Model ML
- Chaz Englander says founders should never announce a raise before they have raised anything, because the first check usually comes from someone they already know.
- Englander says Fat Lama's SPAC exit process cost over $500,000 in legal fees and six to nine months before a buyer that kept calling finally acquired the business.
12 Feb · 50 min
Adam Neumann Returns, SV Spies, AI Robots Rise | April Startup News w/ Jack Kuveke
- Adam Neumann has raised $100m at a $2.5bn valuation for a residential property business resembling WeWork's model, and Jack Kuveke says venture investors back him because they do not really care about criticism.
- Jack Kuveke says Deel placed an ex-Rippling employee inside Rippling who took sales and marketing information from Slack channels, and says the Deel CEO then fled to Dubai.
8 May 2025 · 40 min
How Wiz grew to $500M ARR in 4 years—& could exit to Google for $23B (largest VC-backed exit in history)
- Pablo Srugo says Wiz reached about $500m in ARR in four years, and Google is reportedly in talks to buy it for $23bn, the largest venture-backed startup acquisition ever.
- Srugo argues the reported deal implies roughly a 40x revenue multiple in a market no longer hot, versus about 15x for Microsoft and 5x to 10x for Google and Meta.
18 Jul 2024 · 11 min
ChatGPT just hit $3B in ARR—here’s why Sam Altman is a strategic genius.
- OpenAI is reportedly generating $3.4bn in annual recurring revenue, roughly double its level six months earlier and up from almost nothing before ChatGPT.
- Host Pablo Srugo argues Sam Altman's strategy is about positioning rather than predicting the future, citing Paul Graham's call Altman the best strategist he has ever worked with.
13 Jun 2024 · 10 min
Reddit hit 1M users in 1 year. The key was listening to users—& not doing what they said. | Reddit CTO & Founding Engineer Chris Slowe
- Chris Slowe, Reddit's first employee, says Reddit had immediate product market fit and grew almost entirely by word of mouth.
- Condé Nast acquired Reddit on October 31, 2006, pitching that it could monetise content the site attracted, while advertising was barely a side thought.
10 Jun 2024 · 53 min
She quit her job without a startup idea. Then built a $550M startup from a bad dentist appointment. I Wardah Inam, Founder of Overjet
- Wardah Inam says she quit her job and shadowed dentists, finding through data that underdiagnosis is more common than overdiagnosis, because dentists lack tools rather than will.
- Overjet funded its first year from Inam's savings, a parental house down payment check, and a dentist's check, while an angel told her only 2 percent of female founders get funded and suggested a male CEO.
3 Jun 2024 · 29 min
Ex-Squarespace CEO on how to sell to SMBs, build tight feedback loops, & stay close to customers even after raising $200M+ | Dane Atkinson, Founder of Odeko
- Dane Atkinson warns that founder desperation tied to the VC cycle can turn a failing product into one its founder keeps forcing.
- SumAll reached about half a million small businesses yet heavy free usage never converted to paying customers, a lesson Atkinson says founders often miss because ego mistakes free usage for winning.
27 May 2024 · 44 min
He built Uber for parking & exited. Then raised $100M+. Here's his formula for finding product-market fit. | Shmulik Fishman, Founder of Argyle
- Shmulik Fishman says Argyle's first paying customer, Level Goals, paid $1 per verification, and Argyle had no paying customers until late 2019, a year after founding in 2018.
- Fishman argues Argyle sells better, faster, cheaper versions of services businesses already pay for, so buyers need no new budget, while pilot customers should use the product free during design.
20 May 2024 · 38 min
COVID nearly bankrupted him. Then with AI he grew from $0 to $25M ARR in 4 years. | Andrew Lockhead, Founder of Stay22
- Stay22 fell from about $2m in annual revenue before Covid to near zero overnight, then rebuilt to roughly $2m a month.
- Airbnb dropped Stay22 in March 2021, a serious loss since Airbnb had represented about 72% of its links.
13 May 2024 · 41 min
He raised $11M off a deck. Here's how he launched Clumio & grew 4x to over 8-figures in ARR. | Poojan Kumar, Founder of Clumio
- Poojan Kumar says he raised a $7m Series A for PernixData on a PowerPoint deck, backed by nearly 15 years of enterprise experience and fewer than 10 targeted investors.
- Kumar says Clumio should be all engineering and product, around 15 to 20 people, with sales starting only after alpha and beta signals show repeatability.
6 May 2024 · 31 min
He quit his cozy Google job & ignored lean startup advice— then grew to $3M in 1 year. | Arvind Jain, Founder of Glean
- Arvind Jain left a decade at Google and Rubrik to build Glean after finding no enterprise search product to buy for Rubrik's own knowledge-sharing problem.
- Jain skipped market sizing and customer validation, sending thousands of low-response LinkedIn messages and deliberately not charging for two years, rejecting the Eric Ries Lean Startup playbook.
29 Apr 2024 · 30 min
5 months in, Snapchat had only 127 users. Here's how Evan Spiegel found product market fit w/ Jeremy Liew (Partner at Lightspeed and Seed Investor in Snapchat)
- Jeremy Liew made Lightspeed's first Snapchat investment in 2012, buying 10% for just under $500,000 when the company was valued near $5m.
- Snapchat grew organically through teens at schools that blocked Facebook, rising from 127 users in August 2011 to 100,000 daily users by April 2012.
22 Apr 2024 · 39 min
He gave up on chasing unicorns. Now he earns $500K+/year from his 3-person startup. | Rand Fishkin, Founder of Moz & SparkToro
- Rand Fishkin argues venture capital suits only about 5% of startups, while bootstrapped companies more reliably get founders to a $10m exit.
- Rand Fishkin says Moz's board wrongly thought SEO was tapped out, and he later stepped down as CEO after a bout of depression, rating his exit a four out of ten.
15 Apr 2024 · 49 min
This solo founder bet on AI 7 years ago. Now he has 5,000 customers & $115M raised. | Dylan, Founder of Assembly AI
- Dylan, founder of Assembly AI, says he writes a private document of every expected investor objection with lengthy answers to stay sharp on competitive and market questions.
- Dylan says a YC partner argued Assembly AI was competing with a Google product manager navigating internal politics rather than with Google itself.
8 Apr 2024 · 31 min
He raised $275M in the last 3 years. His 'boring' B2B startup is now a $1B unicorn. | Andrew Butt, Founder of Enable
- Andrew Butt says Enable's rebate software took off only after a 2013 Silicon Valley study tour convinced him to abandon services for a product.
- Enable had about 20-something customers and $2.5m in ARR by late 2019, and Butt says he would have shut down the services business sooner.
1 Apr 2024 · 42 min
Alex sold couches online before IKEA did. He grew to $40M in revenue and exited for millions. | Alex Back, Co-Founder of Apt2B
- Apt2B, founded by Alex Back, grew to about $40m in revenue before a Midwest brick-and-mortar chain of roughly 30 stores acquired it in 2018.
- Back says Apt2B's consistent revenue came from a promotional calendar repeating every six to eight weeks and a direct link between discount depth and sales.
25 Mar 2024 · 39 min
For 5 years he struggled to get traction. Then with AI he grew 12x— in 1 year | Scott Stevenson, co-founder of Spellbook
- Scott Stevenson says Spellbook, originally Rally Legal, grew from about 100 law firms to nearly 2,000 after the team pivoted to AI drafting.
- The team built its first AI autocomplete for lawyers in about two weeks on evenings and weekends, launching as a Microsoft Word add-in before ChatGPT arrived in 2022.
11 Mar 2024 · 41 min
Every VC Rejected Him. So He Bootstrapped From $0 to $10M in 3 years | Kyle Braatz, founder of Fullscript
- Kyle Braatz says Fullscript went from a failed US launch to a healthcare company after realizing practitioners spent 30 to 40 minutes building treatment plans by hand.
- Fullscript made its platform free for practitioners and added e-prescribing of supplements to patients' phones, which Braatz says lifted conversion from about 17% to over 50%.
4 Mar 2024 · 38 min
How to Raise a Round in 2024 w/ Lee Silverstone (3x Founder)
- Global angel and seed funding fell from about $4.5bn in January 2022 to about $2.1bn in January 2024, with investor FOMO gone and rounds smaller and slower.
- Pablo Srugo says post-money SAFEs dilute founders more than anything else, using a hypothetical where the founder ends with 50% instead of 58% under pre-money SAFEs.
20 Feb 2024 · 28 min
He Almost Went Bankrupt TWICE...Then exited for $30M. w/ Canvaspop CEO Nazim Ahmed
- Nazim Ahmed says he nearly went bankrupt around 2009 after taking a line of credit on his house to build Canvaspop's in-house back-end system.
- Canvaspop stalled near $8m in revenue before a 2017 institutional raise, board formation, and OKRs returned growth to $15m.
5 Feb 2024 · 48 min
How a Viral Ad drove Millions in Revenue and $55M In Funding w/ Walnut CEO Yoav Vilner
- Yoav Vilner says Walnut's Product Hunt and LinkedIn launch drove its waitlist, which grew to 700 people before its seed round.
- Vilner says the We are Prospect video drew millions of organic LinkedIn views without mentioning Walnut, showing that buyers' shared frustration can sell a product.
29 Jan 2024 · 37 min
How to Bootstrap from 0 to Millions in Revenue w/ Ilya (CEO & Founder, Vanhack)
- VanHack founder Ilya says the company pivoted from an expensive in-person coding-and-relocation program to a recruiting business after 50 landing-page signups in one day.
- Ilya quit Best Buy to run VanHack full time on December 31, 2015, after its English course out-earned his day job.
15 Jan 2024 · 32 min
5 Steps to PMF with Rob
Pablo Srugo and Rob revisit the five steps to product-market fit from an earlier episode, adding stories and debating where the steps break down in practice. They cover research, focus, value over growth and pivoting, using examples from founders and companies such as Wapa, Bolt and Potluck.
8 Jan 2024 · 43 min
The Best Episode of Season 1 - How Ada Pivoted to a $1B+ Valuation w/ Mike Murchison (Founder & CEO)
- Mike Murchison and cofounder David spent most of a year working as full-time customer service reps for seven companies before building Ada, the no-code AI chatbot now valued at over $1bn.
- Murchison says the team proved the value manually first, avoiding code, and then built software that replicated their own work, with managers unable to tell the difference in responses.
2 Jan 2024 · 38 min
How I lost $6M, Why hype means nothing, Plus a dozen other lessons from our last startup
- Pablo Srugo's last startup, Gym Track, cut its staff from 30 to 8 after a failed near acquisition, and Rob Woodbridge became CEO to lead the turnaround.
- Lee Silverstone calls customer discovery the founders' central mistake, arguing that their letters of intent from gyms carried little weight and the team mostly sought validation for what it had already decided to build.
11 Dec 2023 · 1 h 7 min
Why every founder needs to Be Like Knight | Rob & Pablo Series
- Pablo Srugo argues constraints give founders power, saying Phil Knight grew Nike only as fast as he could fund it and might not have existed had he raised money early and overhired.
- Rob Woodbridge notes Nike lost $57,000 in one year, which shocked its board, and argues a business cannot lose money and survive.
27 Nov 2023 · 47 min
How to (Accidentally) Build a Unicorn
- Pablo Srugo argues services businesses carry less demand risk than tech startups because the demand already exists, making them a smart first venture for founders.
- GoBolt grew by targeting only university students in specific postal codes, and Srugo says narrow focus lets founders tailor every message to one customer.
13 Nov 2023 · 14 min
Mark Ang, Founder of GoBolt | How to Pivot to Product Market Fit
- Mark Ang says Second Closet hit $20,000 in monthly recurring revenue within two weeks after spending just $500 on guerrilla marketing around the University of Toronto.
- Business users at Chanel, WeWork and BMW started using the consumer storage service for their own logistics, prompting GoBolt's pivot toward commercial work and fulfilment software.
6 Nov 2023 · 50 min
Andrew Tai, Founder of MotoInisght | How to Pivot to Product Market Fit
- Andrew Tai says Unhaggle's consumer car-buying marketplace stalled because it lacked capital to fight Autotrader and automakers' advertising and dealers left without immediate value.
- Tai pivoted to selling vertical SaaS to dealers and automakers, who became design partners whose payments financed MotoInsight's growth while the company stayed bootstrapped.
23 Oct 2023 · 42 min
Ron Spreeuwenberg, Founder of HiMama | How Proper Customer Discovery Leads to Product Market Fit
- Ron Spreeuwenberg says he called ten daycares from the yellow pages without selling anything, and 70 to 80 percent were intrigued, validating HiMama's idea before building.
- Ron Spreeuwenberg approached early research as a researcher rather than an entrepreneur, using in-person visits and surveys to decide whether the idea was worth a decade of his life.
10 Oct 2023 · 35 min