A Product Market Fit Show | Startup Podcast for Founders

There are a few things harder when building startups than getting your first few customers. When you're on a standstill, getting momentum is incredibly hard. Going from zero to one takes an incredible amount of effort—you have absolutely no credibility, no proof points.

So to help you out I went through 24 ways of getting your first customers using 24 different examples from this show.

Why you should listen:

• Figure out how to land your first few customers. You are guaranteed to find at least one example that works for you.

Keywords
customer acquisition, startup strategies, community building, persistence, experimentation, free services

Timestamps
(00:00:00) Intro
(00:01:35) Stay22 - Pay your Customers
(00:02:25) Reddit - Creating your Community
(00:02:58) Rappi - Seeding Supply
(00:04:04) Wattpad - Seeding Demand
(00:05:05) Cameo - Finding Someone With an Audience
(00:05:43) Noibu - Showcasing the Value of the Platform
(00:06:41) Bridgit - Showing up in Person
(00:07:24) Rewind - Attaching to an Ecosystem
(00:08:36) Clio - Adding Friction to the Funnel
(00:09:06) Wealthsimple - Lunch & Learn
(00:09:29) Athennian - Classic Customer Discovery
(00:10:00) Carbon Robotics - Presales from Customer Discovery
(00:10:34) StackAdapt - Creating Custom Software
(00:11:21) ApplyBoard - Identifying Power Users
(00:12:27) Forma AI - Sheer Force of Will
(00:15:01) Blockthrough - Starting with an Obvious Problem
(00:16:25) GoBolt - Finding Problems Close to You
(00:17:08) Shopify - Building a Waitlist & Showcasing the Product
(00:17:43) Fullscript - Cold Emailing
(00:18:30) Spellbook - Running Experiments Exceptionally Quickly
(00:19:27) Legion - Finding a Design Partner
(00:20:18) Knak - Consulting
(00:20:54) Dabble - Building Distrobution
(00:21:55) Zeffy - Making the Product Free

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Ankit left his job as a VC to launch a Voice AI platform—back in 2018! It wasn't the voice AI of today. The first demo sounded like a robot. But still, he convinced large enterprise customers in the healthcare space to try it out. He found a highly manual, call intensive workflow in the back office and autoamted it using AI.

Years later, he's raised $102M and has dozens of large $1M+ enterprise customers using the product. He talks about how he started it, how he saw the AI opportunity so early on, and how he found a way to lock in champions that pushed his product inside large enterprises.

Why you should listen:

• Why the search for product-market fit never stops.
• How to build trust with enterprise customers.
• How to get champions to fight battles for you and win enterprise deals.
• Why even successful startups are never straight lines up and to the right.

Keywords
product-market fit, AI in healthcare, automation, conversational AI, startup challenges, scaling, founder advice, technology evolution, compliance, trust in AI

Timestamps
(00:00:00) Intro
(00:02:01) How it all started
(00:06:29) Automating Insurance Calls
(00:16:37) Landing the first customers
(00:22:02) Giving your persona phone number to early users
(00:27:43) Landing large enterprise customers
(00:33:45) Getting Early Adopters to Believe
(00:36:34) Finding Product Market Fit
(00:38:04) One Piece of Advice

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Marty and his co-founders lived full-time in their office for several months. They worked on their startup 24/7. To come up with the idea, they messaged 120 potential customers every day for 3 months.

Originally, when they pitched YC they were told their idea would never work. YC said they'd seen it several times and it was destined to fail. So in 2 weeks Marty landed a customer and built a product-- and YC let him in. He went on to raise a $3M seed round from General Catalyst in 6 days and later a $17M Series A from a16z in 14 days.

We go deep into how to come up with massive ideas, how to get to product-market fit, and how to quickly fundraise from tier 1 VCs.

Why you should listen

• Why all 3 founders living in the office was the best decision they ever made. 
• How to raise a seed round in 6 days and a Series A in 14-- all from tier 1 VCs. 
• How to leverage LinkedIn to get exposure and lots of leads. 
• How to get more mindshare from your employees.
• Why Pylon has almost no meetings.
• How to come up with an idea using both top-down and bottoms-up processes.

Keywords
founders, startup, customer support, Pylon, co-founders, omnichannel, B2B, venture capital, product market fit, entrepreneurship, startup, Y Combinator, fundraising, product development, market trends, customer support, AI integration, team dynamics, venture capital, entrepreneurship

Timestamps

(00:00:00) Intro
(00:01:35) Why he chose to sleep in the office
(00:07:11) Project Management instead of People Management
(00:11:24) How it all started
(00:23:33) Cold Messaging Potential customers
(00:28:02) Finding the Trend
(00:35:49) Building V1
(00:38:32) Getting into YC as ChatGPT Comes Out
(00:42:37) Why fundraising is a "social game"
(01:01:21) Raising Series A from A16

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I interviewed Martin on the keynote stage at the SaaS North conference. Here is the audio version. Martin built Applyboard into a $4B unicorn doing $100M+ in ARR. He left and started a new startup called Passage— and raised a $40M seed round.

He talks about 100-hour weeks, hiring exceptional talent, why smaller teams can outperform—and why he decided to start all over again.

Why you should listen:

• Why great founders thrive in high-stress situations-- on "the edge of failure" as Martin calls it.
• How to make your first hire. 
• Why you need to go all-in and work crazy hours to build a unicorn.
• Why Martin thinks it's key to never give up, even in tough times, as cliche as it might sound.
• The importance of creating a positive environment to attract good people.

Keywords
entrepreneurship, education, immigration, impact, startup, Passage, ApplyBoard, perseverance, business model, founder journey

Timestamps
(00:00:00) Intro
(00:03:54) Getting Into Coding
(00:06:48) Accidentally Making Applyboard
(00:10:41) Starting startup #2
(00:17:19) Raising the Biggest Seed in Canada with Only 20 Employees
(00:20:07) If You Can't Outsmart Them, Outwork Them
(00:23:21) Getting the First Software Developer
(00:25:48) One Piece of Advice

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Jon started a sports betting app 4 years ago-- now he does $150M in revenue and $1B in betting volume. AND he's profitable. In his first year alone , he did $10 million in revenue.

He took a year to build the app and as soon as he launched it, it took off. He did $10M in revenue in his first year.

Honestly, it sounds too easy. But the reason it worked is because, as he shares on the episode, he'd spent 7 years in research mode. He'd spent years building a marketing agency in the sports betting space. He not only understand the market, the customers and the product, he'd also built a distribution machine and knew exactly how to get in front of users.

Here's how it happened.

Why you should listen
- Why distribution is the difference between success and failure
- How spending a long time in research mode can make go-to-market much faster
- Why simple product difference can lead to huge differences in outcomes

Keywords
sports betting, Dabble, entrepreneurship, product-market fit, startup journey, social betting, technology, marketing, revenue growth, challenges

Timestamps

(00:00:00) Intro
(00:01:49) Getting Into Sports Betting
(00:04:22) Before Dabble
(00:08:08) Starting Dabble & First Steps
(00:10:55) The Initial Vision
(00:17:55) How Sports Betting Works
(00:24:26) Nearly Going Bankrupt
(00:27:53) Building the App
(00:31:23) Launching
(00:35:47) Revenue Timeline
(00:38:28) Finding Product Market Fit
(00:41:48) One Piece of Advice

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Yanni started building in crypto back in 2013, when you could buy one Bitcoin for $20. At one point, he was playing poker games and betting 1 bitcoin each round!

He built an extension that let people use bitcoin to buy anything, anywhere on the internet. Then he pivoted to building the first on ramp for bitcoin. And finally, pivoted into Wyre, which was like Stripe for Crypto, a platform to let developers build Web3 apps.

In a couple of years he scaled it from nothing to a $90M run rate. In late 2021, he started working on an exit with Bolt. By mid 2022 the deal was signed. The company was to be sold for $1.5B.

Yanni would make hundreds of millions of dollars himself.

And then, at the absolute last minute, the world changed. Stocks fell, crypto plummeted— and the deal fell apart.

Startups are often one call, one customer or, in this case, one day away from complete success—or total failure. That’s the game you’re playing. 

And there are few stories better than the one you’re about to hear.

Why you should listen
- Why if you want to be a founder you can't avoid taking punches to the face

- How Yanni found Bitcoin just a couple of years after it was started

- Why it often takes multiple twists and pivots to find real PMF

- How acquisitions tend to happen and why they can always fall apart 

Keywords
startup, acquisition, Bitcoin, Web3, entrepreneurship, crypto, payment processing, innovation, technology, business, crypto, infrastructure, product-market fit, Web3, acquisition, startup challenges, fintech, business growth, developer support, market downturn


Timestamps
(00:00:00) Intro
(00:01:50) Buying Bitcoin in 2013
(00:04:48) Creating a Hacker House in San Francisco
(00:19:08) Creating Crypto Wallets
(00:26:41) Becoming Wyre
(00:33:56) Making the Decision to Go All In on Crypto
(00:41:18) The Acquisition that Didn't Happen
(00:47:33) Learning from All the Mistakes
(00:52:03) Some People are Builders

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Aaron was Director of Product at Amazon, VP Product at Twilio, PM at Facebook and Twitter. Now he’s head of product at Deel where he reports directly to the CEO. Deel was founded in 2019— now, just 5 years later, it’s worth $12B and raised over $650M. 

We go deep on what it takes to build world-class products, how early-stage founders can balance customer feedback, vision and data, and how the best product leaders are leveraging AI today.

Keywords

productivity, AI, product development, user experience, product management, customer feedback, product market fit, technology, innovation, startups

Why you should listen

• Why you’re better off trying to enhance than replace with AI— at least today.
• Why you need to deeply understand your users to build products they truly love. 
• How to avoid the customer feedback trap and only build features that move the needle.
• How and when to hire your first product manager. 
• What makes a product truly great 

Timestamps:

(00:00:00) Intro
(00:10:25) AI Solves the Informational Retrieval Problem
(00:14:54) AI Agents Aren't Real Yet
(00:18:12) Signals that Could Lead Towards to PMF
(00:23:04) Finding the Customers Need
(00:25:17) Hiring Product Managers
(00:28:00) Difference Between an excellent Product vs an Okay One
(00:34:17) Prioritizing Bug Fixing vs Feature Requests from Existing Users

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Description

Tate started doing commercial fishing at 16. He took that money and started lending it— on Craigslist! By 23 years old, he’d lent out $250,000. Then he found out about cash advances, and decided to start ZayZoon, a platform to help employers pay their employees faster.

Tate was one of the early pioneers of the entire Earned Wage Access space. By partnering with payroll companies and employers, ZayZoon lets employees access their earned wages faster.

It took Tate and his co-founders 4 years to get to their first million of ARR. And as soon as they felt they had it,  revenue crashed 60% in a quarter. The team got things back on track and since then has grown from 20 to 200 employees—  revenue is now closer to $100M than $10M. 

Here’s the story.

Why you should listen:

• Why you need to be all-in at the early stages
• How to arm channel patterns to sell your product
• How to re-position your product so it’s clear you solve customer problems
• Why it can take years for a new category to take off

Keywords

entrepreneurship, lending, FinTech, earned wage access, startup journey, mentorship, risk management, payroll integration, business challenges, market challenges, growth strategies, employer empowerment, product-market fit, exponential growth, timing, customer engagement

Timestamps:
(00:00:00) Intro
(00:01:25) Lending Money on Craigslist in Highschool
(00:13:06) The Origin of Zayzoon
(00:19:18) The Next Step After the Aha Moment
(00:24:44) Problems Starting Off
(00:29:08) Launching First Payroll
(00:30:58) Fundraising
(00:34:11) Making the Product Easy to use 
(00:45:32) Hitting a Million Dollars
(00:48:53) Why timing matters
(00:53:34) Finding Product Market Fit
(00:54:27) One Piece of Advice
(00:56:29) How all in were you?

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Zeffy is one of my biggest misses so far. I met Francois 3 years ago when he was raising his $3M seed round. But I passed.

They were at ~$500K in revenue at that point. In the last 3 years, they've grown 30x. Clearly, I missed out.

But it's been a long road for Francois. Before he got to the current idea, he had to make 3 pivots, including building a marketplace and selling to schools. 

Finally he landed on what Zeffy is today,  a fundraising platform for nonprofits. The crazy thing is that it's absolutely free to use. They make all of their money, which is now in the tens of millions in revenue a year, from tips. Voluntary tips that are given by donors while they donate to the nonprofits who use Zeffy's platform.

It's not an easy model to wrap your head around, but it's working in a big way.

Check out the platform at zeffy.com

Takeaways

• How to use new revenue models as differentiators.
• When to use sales-led vs marketing-led growth. 
• Why the one and done funding model can work so well
• Why getting to profitability gives founders so much power. 

Keywords
fundraising platform, nonprofits, product market fit, startup growth, profitability, marketing strategy, trust building, talent density, donation model

Timestamps
(00:00:00) Intro
(00:02:49) The Origin of Zeffy
(00:05:56) Gaining the Trust & Cold Calling
(00:08:52) Having a Sales Team Not Trying to Get Money
(00:13:21) Zeffy's Growth Timeline & Raising
(00:15:35) Google Ads Changed the Game
(00:18:54) The Mindset After Raising the Seed
(00:21:50) Staying Conservative When Recruiting
(00:24:05) What Makes Zeffy Unique
(00:27:38) Finding True Product Market Fit
(00:28:37) One Piece of Advice

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In 2014, Ian launched a simple product: it let social media marketers buffer Instagram posts. It was originally a hackathon project. But it quickly gained users. So he and his co-founders went all in.

They raised just one small seed round. His main competitor, HootSuite, raised over $300M. In spite of that, he built a $40M ARR business that sold for well over $100M.

Here's the story of how it all happened. And why there's an option besides bootstrapping and raising round after round: it's called the one & done.

Why you should listen:

• Why you won't know if people love your product until you charge them. 
• How to use content marketing to drive inbound traffic. 
• How user experience can be a big differentiator even in a competitive market.
• What the acquisition process is like and why it often drags on. 

Keywords

startup, product market fit, user feedback, monetization, content marketing, growth strategies, social media management, entrepreneurship, user acquisition, pricing strategy, startup, growth, competition, user experience, influencer marketing, acquisition, exit process, founder advice

Timestamps:
(00:00:00) Intro
(00:03:05) "Ian's dumb ideas"
(00:07:27) Hackathons
(00:10:41) Finding a market
(00:13:30) Early feedback
(00:17:50) The growth curve
(00:21:08) Turning on pricing
(00:26:35) A seed strapper
(00:31:58) Focusing on small and medium businesses
(00:38:24) Being well positioned
(00:43:19) Bough by private equity
(00:47:50) Relief
(00:50:59) A new project and a piece of advice

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