Dave Salvant and his co-founder Songe had no technical background, no barbershop experience, and were burning through their seed money. With only $60,000 left in the bank, they made a desperate "all-in" bet: they used 30% of their remaining cash to buy a barbershop in New York City.

In this episode, Dave reveals how "becoming the customer" by operating a physical shop was the secret to building Squire, now a $750M all-in-one platform for barbershops. We discuss the reality of "hand-to-hand combat" sales, paying barbers cash to stay online during outages, and the journey from a struggling idea to Y Combinator and beyond.

Chapters:

(00:00) - The "Make or Break" bet: Spending the last $60k

(04:01) - Whiteboarding ideas at Columbia University

(08:23) - Validating the idea without industry expertise

(16:29) - "Uber for Barbers": Why the initial model failed

(21:11) - Buying a physical barbershop to fix the software

(28:40) - Surviving the fundraising struggle and Y Combinator

(33:14) - How to manufacture Product-Market Fit

(40:56) - The Sacramento Story: Flying cash to barbers during an outage

Referenced:

• Squire: GetSquire.com

• Guest: Dave Salvant on LinkedIn

• Careers: careers.getsquire.com

About Before It Clicked:Before It Clicked is the playbook for going from aspiring founder to business owner. Hosted by Sunny Rekhi, we explore the unpolished journey of how great ideas are born—and teach you how to replicate that discovery process for yourself.

Keywords: SaaS, Vertical SaaS, Startup, Product Market Fit, Y Combinator, Venture Capital, Barbershop, Entrepreneurship, Pivot, Squire

Vouch is now a $550M company, supporting 6,000+ high-growth companies. But they did it by rejecting the core tenets of startup wisdom.

On this episode of Before It Clicked, we dive into the early, messy days of Vouch with co-founder Sam Hodges. In a world that preaches "move fast and break things," Sam reveals why his team adopted the "Fat Startup" strategy—a calculated, capital-frontloaded approach necessary for winning in the heavily regulated, capital-intensive insurance market.

Inside the interview:

• The Origin Story: How a problem at Sam's previous company led to a thesis-driven effort to disrupt the $1.2 trillion insurance industry.

• Contrarian Strategy: Why Vouch raised a massive Series A before full launch, strategically deploying capital and hiring deep domain experts on day one to gain regulatory credibility.

• The "Wizard of Oz" Reality: The scrappy truth behind their early success: Sam shares the wild detail that for the first 30 policies, an engineer was manually updating database settings in real-time to "bind" the insurance.

This is a must-listen for any founder tackling regulated industries like FinTech, HealthTech, or HardTech who needs a proven alternative to the lean startup playbook.

Chapters:

00:00 - Intro: The "Wizard of Oz" backend 

02:00 - Vouch Today: 6,000+ customers & billions in value 

03:31 - Origin Story: Why insurance was the "broken" layer 

06:42 - Planning Phase: Why they couldn't just "iterate" 

13:56 - Unit Economics: Validating profit before writing code 

18:10 - Hiring: Why Vouch hired a Chief Insurance Officer on Day 1 

23:51 - The controversial decision to go Direct-to-Startup 

25:46 - The "Utah Wedge": Choosing the right launch state 

27:41 - The "Fat Startup" Thesis & Raising $24.5M Pre-Launch 

32:14 - Business Models: MGA vs. Carrier vs. Broker 

41:21 - Tech Debt: The cost of building a monolith too early 

45:31 - The Innovator's Dilemma: Why legacy carriers couldn't copy them 

52:43 - Launch Reality: Manually binding policies & COVID 

57:05 - Navigating the 2022 downturn & SVB collapse 

01:02:36 - The Pivot: Selling the underwriting arm to Hiscox

👋 CONNECT WITH US:

👉 If you enjoyed this episode, please follow the show and leave a 5-Star rating! ⭐️⭐️⭐️⭐️⭐️

• Follow the Pod on X: x.com/beforeitclicked

• Follow Sunny Rekhi: x.com/sunnyrekhi

• Check out Vouch: vouch.us

Resources Mentioned:

• Vouch: vouch.us

• Scale up your startup insurance: vouch.us/scale

Two founders with zero healthcare experience built the first iPad-native EHR app… and found explosive PMF even though they started DrChrono before the iPad existed.

In this conversation, Daniel Kivatinos (co-founder of DrChrono) walks through how an outsider team broke into one of the most regulated, slow-moving industries and still reached a nine-figure exit. We cover:

1. Why Daniel and Michael Nusimow jumped into healthcare with no healthcare background
2. How they iterated with real doctors and built a product people actually loved
3. The bet on iPads before they existed
4. Lessons on intuition, fast iteration, founder psychology, and surviving years before PMF

If you're a founder navigating uncertainty, doubting your idea maze, or trying to break into a legacy industry—this episode will give you the blueprint for trusting your intuition and building your way to product-market fit.

Chapters:

(00:00) Intro — who Daniel Kivatinos is & what DrChrono became 

(02:54) What DrChrono looked like at exit (thousands of doctors, millions of patients)

 (07:38) Daniel’s pre-DrChrono startup journey & realizing he wants his own company 

(20:20) Choosing healthcare without experience & ignoring strict “founder–market fit” advice 

(23:56) Bootstrapping with $50k in the bank and no investors

(26:35) Version 1 — building a scheduling calendar doctors actually use 

(39:10) From scheduling to full electronic medical records & first paying customers 

(43:53) The empty NYC “incubator” & discovering the iPhone / iPad opportunity 

(47:48) One day a week on iPad — taking a controlled but non-obvious bet 

(55:31) iPad launch day, surprising battery life & the true product-market fit moment 

(57:08) Emailing Y Combinator while almost out of runway 

(59:23) Alexis Ohanian visits their four-startup “hub” & invites them to YC 

(1:06:23) Filtering customer feedback & trusting founder intuition

(1:12:30) Dealing with heavily funded competitors & why speed matters more

 (1:18:02) Starting ⁠⁠⁠JustPaid and what he’s building now 

(1:24:00) Can outsiders still win today? 

(1:27:34) Closing advice: momentum, risk & not over-analyzing

Disclosure: the acquisition price comes from EverCommerce’s public SEC disclosures, not from Daniel, who is under NDA.

When Michel Tricot left his job in 2019, he didn’t have an idea yet — he just knew he wanted to start a company.

Over the next year, he and his cofounder cycled through ideas: remote-controlling self-driving cars, fintech for gig workers, a healthcare data-sharing platform, and a marketing analytics product that actually had paying customers… until COVID exposed it as a “nice to have,” not a must-have.

Instead of forcing mediocre product–market fit, they did the hard thing: admitted they had the right team, wrong idea, and went back to the whiteboard. From there, the team ran weekly Zoom sprints, ranking ideas by founder–market fit, team excitement, and how painful the problem sounded in real interviews.

The pattern that kept resurfacing: everyone was struggling to move data reliably between tools. That insight became Airbyte — an open-source way to build and share data connectors, now used by thousands of companies and valued at around $1.5B.

I’m Sunny Rekhi, host of Before It Clicked. In this episode, Michel walks me through:

• The dead-end ideas before Airbyte

• How they ran structured weekly idea sprints

• The moment he realized “we have the right team, wrong idea”

• How the open-source Airbyte thesis finally clicked

• Why agents are the next big consumer of data

Chapters

• (00:00) Intro & where Airbyte is today

• (05:07) How Michel thinks about starting a company & idea validation

• (07:22) Pivot #1: remote-controlling self-driving cars

• (10:44) Pivot #2: fintech for gig workers (the YC idea)

• (16:06) Pivot #3: healthcare data-sharing & discovering “data movement”

• (21:22) Dexterity/DataLine: marketing analytics & the COVID “vitamin vs painkiller” moment

• (27:18) Realizing it’s the wrong idea & deciding to pivot again

• (30:40) Weekly Zoom whiteboard sprints & how they ranked ideas

• (40:17) Building an open-source Segment prototype → the Airbyte insight

• (46:50) Airbyte v1, design partners & early traction

• (55:25) Community explosion, fundraising & Airbyte’s future with AI agents

Most founder stories jump straight to the win. This one doesn't.

Nikhil Gupta, cofounder and CTO of Vapi, spent 5 years grinding through 12 different pivots before landing on the idea that raised at a $130M valuation. We dig into the false starts, the moments he almost gave up, the pivot that finally clicked, and the tactical decisions that separated failure from hypergrowth.

You'll hear:

• How to know when to pivot vs. when to persist
• How his ideation improved over 12 ideas
• What changed in the pivot that actually worked
• Timeline of the 5-year journey (the real one, not the polished version)

This is the story before the story—no mythmaking, just the messy path to product-market fit.

Chapters:

• (⁠00:00⁠): Cold open — “What is wrong with me?”
  (⁠00:19⁠): Intro — show setup & where Vapi is today (400k devs, $130M Series A, 6→45 people)
  (⁠02:16⁠): Meeting Jordan at Waterloo, dropping out & deciding to build a company
  (⁠06:13⁠): Early ideas: ETF “playlist of stocks” investing app
  (⁠07:54⁠): Friend CRM & betterfriend.me — first tarpit consumer idea
  (⁠10:33⁠): COVID learning app that got them into YC
  (⁠17:46⁠): Getting into YC, moving into a house & pre-batch meltdown
  (⁠19:30⁠): Idea framework: frequency, intensity & willingness to pay
  (⁠21:06⁠): Discovering the “join my next meeting” button
  (⁠25:21⁠): Product Hunt launch, Reddit “YC is funding button companies” & early revenue
  (⁠32:29⁠): Two years of experiments: Slack, focus tools & growth hacks that didn’t work
  (⁠42:25⁠): Auto meeting notes — listening to the computer & shipping a notes product
  (⁠45:27⁠): Realizing most users don’t use notes; doctors & wealth managers do
  (⁠47:53⁠): Shutting down a profitable product & moving to SF
  (⁠52:13⁠): AI therapist — Dolores Park airdrops & mental-health market worries
  (⁠1:00:57⁠): Turning the voice stack into an API & helping Hyperbound
  (⁠1:03:37⁠): March launch, virality & why OpenAI’s real-time API didn’t kill Vapi
  (⁠1:09:00⁠): Hiring from the community, getting to ~$4M ARR with 6 people & scaling the team
  (⁠1:16:30⁠): Nikhil’s closing advice