A Product Market Fit Show | Startup Podcast for Founders

Saurav started a Groupon-like offering for SMBs in 2011. He quickly learned it wasn't going to work. He and his team pivoted and started driving leads to suppliers using Facebook ads. It worked and they generated revenue—but they were becoming a digital advertising agency. It wasn't at all what they wanted to build.

So they pivoted again.  They used the cash from that business and built Perkbox. The idea was a subscription-based offering that that gave perks to SMB customers. Telcos started buying it and attaching it to their products to drive sales. Then, they pivoted again, this time moving away from customer perks and to employee perks.

This time, it worked. They grew from $2M in ARR to $14M in just 2 years. They kept growing and hit $36M in ARR. Then he sold the business to PE for $170M.

It took longer than expected. There were more pivots than expected. But it was a huge success.

Here's how it happened.

Why you should listen:

• How to use new social media channels to drive growth.
• How to leverage partnerships to get end user adoption.
• Why having a profitable agency can be a great way to get started.
• Why capital efficiency can be a huge edge.
• Rebranding can help clarify market positioning.
• What it feels like to make $10s of millions in one day.

Keywords
PerkBox, Groupon, startup journey, business model, SMB market, marketing strategies, recurring revenue, partnerships, entrepreneurship, exit strategy, venture capital, entrepreneurship, startups, employee benefits, social media marketing, capital efficiency, business growth, acquisition, rebranding, emotional marketing, lessons learned

Timestamps
(00:00:00) Intro
(00:01:48) The origin of Perkbox
(00:04:52) Going after SMBs
(00:12:16) The Pivot
(00:26:35) Creating Viral Ads
(00:32:28) Demo to Close Rate
(00:40:12) Selling to PE Firms
(00:49:38) A Piece of Advice

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In 2005 most people didn't even have cellphones yet. Those who did used flip phones. That's when Noah started Olo, a webapp to let people pre-order coffee from nearby shops. Users had to login on web, add a credit card, create pre-made orders and then send a text to a preset number when they wanted to pre-order. It was way, way ahead of its time. 

Noah and his team 7 years to hit $1M in ARR. In the meantime, they raised a round with 50% dilution the week before the financial crisis, went on live TV to an audience on 6M viewers and had to pivot from a marketplace to B2B SaaS.

But overtime smartphone penetration increased, on-demand ordering became a trend, and then, one day, Starbucks launched their app. All of a sudden, every single restaurant in the world wanted a way to let their users pre-order.

And there was Noah and his team at Olo.

Today, Olo is a public company worth over $1B and generating nearly $300M in sales. Here's the story of how it happened.

Why you should listen:

• How to use guerrilla marketing tactics to get early growth.
• Why PR can move the needle but not in ways you expect. 
• How to pivot from a marketplace to B2B SaaS.
• Why it often takes much longer than you might hope to hit an inflection point.
• Why fundraising was so hard, even though Olo became a $1B+ public company. 
• Why Noah thinks founders should embrace challenges and adversity.

Keywords
Olo, Noah Glass, entrepreneurship, product-market fit, restaurant technology, mobile ordering, startup journey, business challenges, marketing strategies, innovation

Timestamps:
(00:00:00) Intro
(00:02:20) Building an app in 2005
(00:13:20) The Burn the Boats Moment
(00:16:31) Building A Network Business
(00:26:08) The Cold Start Problem
(00:30:33) A Happy Accident
(00:36:55) Going through the 2008 Financial Crisis
(00:51:20) Finding Product Market Fit
(00:57:20) Blueprint of Values
(01:05:11) Best Piece of Advice
(01:06:08) A Big Milestone

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Frankie lost $10K in a crypto transaction—so he started Staging Labs to find a way to help others prevent crypto scams. He was head of an incubator called Entrepreneurship First and had seen dozens and dozens of founders build startups. He knew exactly what to do—and he did everything right. He found a co-founder, built an MVP, did customer discovery, checked willingness to pay—but he still failed.

The world changed when crypto crashed in late 2022. The people who were originally interseted in paying for crypto insurance nolonger were. And by the time Frankie realized it, it was too late.

Here's how it happened—and how he was able to sell his startup even though the product wasn't working out.

Why you should listen: 

• How to sell your startup even when it's not working out.
• Why sometimes the best ideas come from personal struggles. 
• Why you need to constantly validate willingness to pay.
• Why you can't treat lean startup as a series of checklists.
• The last 10% of execution is often what determines success or failure.
• Partnerships can be a double-edged sword in startup strategy.
• How aligning personal values with customer needs is essential for founders.

Keywords
entrepreneurship, startups, crypto scams, fundraising, product launch, market timing, personal experience, validation, community building, business challenges, willingness to pay, user experience, scams, customer alignment, market cycles, acquisition, strategic partnerships, investor relations, startup lessons

Timestamps:
(00:00:00) Intro
(00:02:25) The Idea & The Origin of Staging Labs
(00:08:07) Next Steps & Pre-Seed Fundraising
(00:13:27) Why you should never depend on partnerships
(00:18:28) How to create urgency
(00:24:55) Pivoting
(00:28:43) Trying to sell the business
(00:35:55) Biggest Lessons Learned

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Hussein's travel startup was doing $10s of millions when COVID hit. His revenue didn't just go to zero, it went negative. There were more customers asking for refunds than new sales. He was 4 months from running out of money.

He ended up making a complete pivot, he changed the company's name from SnapTravel to Super.com. He went from travel to fintech and launched a banking card. It seems like a strange pivot —but through deep research he'd realized what his customers truly needed. They needed more money—not for travel or vacations—but for every day life.

The new card helped customers earn points and rewards, it helped them save on everyday expenses. The pain was so acute and the solution so perfect, that just 3 years later, Super.com is doing $150M in ARR.

Like Hussein said, he got 50 'no's from VCs for every 'yes' he got. He saw his business grow and then crumble over night. He was literally going to zero. 

But he turned it all around. Now he's not just growing, he's profitable now.

And here's how it went down.

Why you should listen:

• How to think from first principles to figure out the right product expansion.
• Why cross-selling is much harder than you think, and how to make it work.
• Why finding an unfair advantage is key to scaling a startup.
• How to use actual customer behavior to understand what customers truly want.
• Why testing and validating ideas through smoke tests is essential.

Keywords
Super.com, SnapTravel, COVID-19, travel industry, pricing strategies, customer needs, market fit, entrepreneurship, AI, business growth, COVID-19, resilience, travel industry, financial innovation, membership model, customer insights, entrepreneurship, investor relations, business strategy, cross-selling

Timestamps:
(00:00:00) Intro 
(00:02:39) The original startup: Snap Travel
(00:08:40) Why a great user interface is a big edge
(00:11:26) How to acquire customers
(00:13:30) When your entire hypothesis is wrong
(00:22:52) Meeting Steph Curry
(00:29:03) Nearly crashing to zero-- and going bankrupt
(00:33:51) Starting over and rebranding
(00:42:42) Creating the Fastest Growing Membership Program
(00:52:17) Finding Product Market Fit
(01:00:00) One Piece of Advice

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When Amplitude launched Mixpanel was the big game in town. They were first to market, had raised more money, and had a well-known brand. VCs passed on Amplitude because it seemed like just another Mixpanel.

Today, Amplitude is a $1.5B public company—they're about 2x bigger than Mixpanel. Mixpanel's marketing spend helped educate the market. But before buying an analytics solution most businesses do market research. That's when they'd find out that Amplitude had several features Mixpanel lacked—and they were much, MUCH cheaper.

It's not cool to win on price, but it works. It worked for WalMart, CostCo, Shein, and it worked for Ampltiude.

Here's the story of how it all happened.

Why you should listen:

• How to use cheaper prices to win in a crowded market.
• Why you often need 12 hour days to win in Startupland.
• Why even massive $1B+ successes often have trouble raising early rounds.
• How pivoting can often be the key to finding real market pull.
• Why big competitors can often be a huge tailwind.
• How to use storytelling to raising bigger rounds. 

Keywords
startups, entrepreneurship, analytics, Amplitude, pricing strategy, market positioning, data processing, voice recognition, technology pivot, competitive advantage, market dynamics, differentiation, product-market fit, storytelling, fundraising, startup challenges, customer relationships, analytics tools, business strategy, entrepreneurship

Timestamps:

(00:00:00) Intro
(00:06:13) A cool demo-- but a bad business
(00:18:36) Why funding was so hard
(00:25:43) Why lower prices are a big differentiator
(00:40:50) Working 24/7
(00:50:35) Product Market Fit

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This first time founder just raised a $38 million Series A. The crazy part is that for all of 2021, 2022, 2023, he had almost no revenue. He spent all that time building and pivoting. Finally he launched in 2024—and it blew up.

I saw his LinkedIn post and his revenue chart doesn't look like a hockey stick... it looks like straight a vertical line. He built a health benefits platform—it doesn't get less sexy than that. And yet, it absolutely exploded to millions in ARR in less than a year.

All because he figured out how to make something that every single company in the U.S. needs, exceptionally simple. 

Here's the story.

Why you should listen:

• Why choosing the right co-founder is the most important thing.
• Why having a mission is crucial to make it through the ups and downs.
• How to listen to and understand customer pain points. 
• Why pivots are not a bad thing, and can actually be the key to crazy traction.
• How to use external deadlines to drive urgency and focus .

Keywords
Thatch, startup journey, co-founders, healthcare innovation, product market fit, venture capital, entrepreneurship, health benefits, business challenges, pivoting, healthcare, startups, product development, market demand, customer needs, external deadlines, product market fit, scaling, company culture, founder intuition

Timestamps:

(00:00:00) Intro 
(00:02:27) Finding the Right Co-Founder
(00:10:23) Why You Need to Go All In
(00:16:20) The Seed Round & Pivoting From the Original Idea of Thatch
(00:30:08) How to use external deadlines to drive focus
(00:37:55) The Growth in 2024 & The Business Model
(00:42:16) The Benefits of Forcing Functions
(00:45:58) How Many Customers are Using Thatch Today?
(00:47:50) Finding True Product Market Fit
(00:52:10) People Didn't Believe in Thatch

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Carta just released their report for Q4 2024. Peter is Head of Insights at Carta, and the person who owns their data practice. We sit down to talk about the largest trends he saw across fundraising, industries, graduation rates and even hiring practices. 

Carta data shows that graduation rates from Seed to A are much lower for companies that have raised a bridge round. We analyze why that might be and what that could mean for early-stage founders.

VCs read and understand all this data. If you want to operate on equal footing— you should too.

Why you should listen:

• The role of AI in the venture capital landscape.
• Why there are a trend of larger funding rounds going to fewer companies.
• Why so much capital is being allocated to AI companies.
• Valuations for seed and early-stage companies are on the rise.
• Why bridges and extensions have become so popular. 
• Why bridge rounds have lower graduation rates to Series A.
• What the data shows about how hiring practices are changing.

Keywords
venture capital, AI, fundraising, market trends, valuations, startup ecosystem, early stage, late stage, investment, venture capital, bridge rounds, seed extensions, startup growth, hiring practices, AI impact, early stage funding, market trends, valuations, exits

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Alon was a hacker for the Israeli Defence Forces' cyber department. There he saw the most advanced methods used in cyber warfare. So when he left, he started IntSights-- a company that helped enterprises defend themselves from cyber attacks.

He was a first-time founder who didn't even know the word 'unicorn'. He made all the mistakes you could make. But he had real, undeniable pull. He grew to $1M ARR in a year and to $4M a year later. By the end of it, he was doing $30M in revenue and exited for $335M.

But when I asked him what it felt like to sell for hundreds of millions, he said it 'felt like emptiness'. Alon is a builder—that's all he wants to do. So he quit post-acqusition and left millions of dollars on the table. Money he was guaranteed to make if he just stayed in his role.

Instead, he started PointFive to help enterprises reduce wasted spend on cloud infrastructure. He know nothing about the space. One year in, he's raised $36M and grown to millions in ARR— even faster than IntSights.

Here's the story.

Why you should listen

• Why Alon felt empty after exiting for $335M.
• Why he left millions of dollars on the table to start a new startup.
• Why the mistakes he made in his first startup helped his second one grow way faster.
• Why he raised $36M in under a year.
• Why true customer pull comes from solving top of mind problems.

Keywords
LinkedIn, video content, cloud cost optimization, engineering responsibilities, startup funding, second-time founders, product market fit, customer traction, entrepreneurship

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Ned had a chance to run Robinhood Asia but he turned it down. Instead, he launched a competitive product. He decided to go B2B and sell to banks and other financial institutions. He locked down a $400K revenue sale before writing a line of code. It seemed easy at first. Overtime, he grew to $3.5M in revenue, billions in assets under management and hundreds of thousands of users. He raised $20M in venture capital.

But then the problems started. Enterprises that paid for large contracts didn't push the product—many had no marketing budgets. In some cases, they shelved the product altogether. The one-time revenue never turned into ARR. Running out of money, he was forced to raise a small bridge and lay off more than half his staff.

He came close—but ultimately, he just wasn't able to recover. He sold off the company for parts and went through a wind down.

This is his story—and the lessons he learned.

Why you should listen: 

• Why the difference between success and failure can be minimal.
• How to balance custom contracts with building scalable product. 
• Why enterprises might not push the product they've paid $100K+ for.
• How to build a strong company culture.
• Why layoffs are the hardest thing a founder will go through.
• When things go south, "the days are long, but the months are short".

Keywords
startup, FinTech, B2B2C, customization, revenue models, marketing, client engagement, leadership, company culture, lessons learned, B2B sales, startup challenges, emotional toll, liquidation, lessons learned

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Jason built a data center company in the 2013. When he exited in 2019, it was the third-largest exit in Canada that year. He'd sold his previous startup and invested 100% of his capital into ROOT. He grew to 10s of millions and exited for 100s of millions.

Now he's invested in over 20 angel-stage startups. He shares the story of ROOT and what he looks for in the startups and founders he backs. 

Why you should listen:

• Why seeing inefficiencies can lead to huge advantages vs competitors.
• How customer concentration can actually lead to a huge success.
• Why the 'Why Now' slide is so important.
• Why Jason values startups can get to free cash flow within 1-2 years.
• How to use the lead to conversation ratio as a leading indicator of PMF. 

Keywords
data centers, investment, entrepreneurship, product market fit, angel investing, business growth, technology, risk management, funding strategies, customer relationships, investment, startup, venture capital, product-market fit, founder advice, business model, cash flow, total addressable market, team dynamics, entrepreneurial hunger

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