Season 1

Raising money seems really easy when you're reading Techcrunch. Then you go out and try to do it and all of a sudden it seems impossible. Especially when you're new to the startup world and know no one. That's exactly what it was like when Aman, the founder/CEO of Procurify, raised his first round.…

Before startup mode, there’s research mode. Many startup stories sound like happy accidents, where founders stumble upon an amazing idea more by chance than by strategy. The reality is the best founders have a deep understand...

There are two types of startups: those that sell into existing markets and those that create new markets. There are ups and downs to both. Selling into an existing market means you have a clear idea of customer needs and mark...

The standard advice is you need to first generate your own demand, and only then look for partnerships to accelerate your business. Another piece of standard advice is you should probably raise a small round early on to hire...

You've launched a startup. Your excitement turns to anxiety as it becomes clear things aren't working out. Some customers are buying but not nearly enough. They like your product, but they don't love it. You realize you don't have product-market fit and are unlikely to get it. You'll need to change…

You have a startup idea. You tell 10 friends and they tell you it's awesome. What does that prove? Unfortunately, not much. Validating your idea requires you to go outside your building and talk to real customers. Not only that, real validation means having customers pay for your product. But how d…

Getting started with a consumer product is HARD. Unlike selling to businesses, you can't just grind it out with cold calling. You'll need to figure out how to get noticed and drive traffic to your site. And getting media atte...

You want to become an entrepreneur. But you're stuck at level 1. How do I come up with an idea? It's not easy. And there's no silver bullet. Matt, the founder of Assent. has built three successful startups: NoNotes, Assent Compliance, and Millions. In this episode, he shares the stories of how he c…

Building a product is the easy part. With the right resources, you can build just about anything. But once you've done that, how do you launch it? How do you get people to know your product even exists? And how do you do it on a tight budget? Jay, the founder of Bold Commerce, has launched dozens o…

Once you have clear traction, once revenue is up and to the right and growing quickly, investors come to you. But what about early on? How do you get people to invest millions of dollars when all you have is an idea? Stephany...

How do you launch a marketplace? How do you get beyond the chicken-and-egg problem? Derrick's answer: Fake it Till you Make it. When launching Drop (a rewards app with millions of downloads), Derrick needed both consumers and brands to join. Instead of going after both at once, he found a way to se…

When you're selling to consumers or small businesses, you can put up an MVP, generate traffic, and watch the money roll in. Not so for enterprise. Enterprise means long sales cycles, procurement departments, security audits, pilots, and many more hurdles. How do you get your first enterprise sale? …

Most startup founders recognize they need advisors. The question is who do you get, how do you get them, and how do you structure it all? In this episode, Darryl shares his framework for how to set up the perfect board of adv...

Running a startup is hard. Doing it alone, especially when it's your first time, can be downright tortuous. Lindsey started off on her own, without much of a network in the startup scene in Toronto. Not only that, as a business type she didn't have the skills needed to build a prototype, let alone …

For even the most successful startups, finding product-market fit is often a long journey and Klipfolio was no exception. Founders often feel that one more feature, one more UI change will get them to product-market fit. The ...

It’s one thing to work hard. It’s another to work hard with a well-researched destination in sight. In this episode of The Product Market Fit Show, Rob Boukine gets real about the mistakes he made in his early days as cofound...

Launching is often thought of as a huge event. Lots of noise, lots of PR. One big bang. For Ray, it's just a series of many small experiments. Ray realized that the number one value prop for a consumer was coverage: when a user opened the app, the majority of merchants that were walking distance ne…

"Ideas are a dime a dozen". Maybe. But executing on a mediocre idea won't get you very far. In this episode, Ray, a multi-time founder who sold his first company to Google, discusses how he came up with the idea for Ritual. I...

If you want to validate an idea, the conventional wisdom is to build an MVP. But even an MVP takes time to build. What if you could validate not only your idea but your entire funnel, without writing a single line of code? Th...

After you've had an idea and validated the problem, it's probably time to build. But how exactly do you decide what to build, how to build it, and how to get end users to actually adopt the solution? Carol is a multi-time founder and she has this process down to a science. On this episode, she shar…

To launch a startup you have to leave your job and spend considerable capital, with no guarantee of success. It involves considerable risk, right? Not for Mike. Mike started Rewind- a company now approaching unicorn status- f...

Why do professional athletes have coaches, but professional entrepreneurs don't? Dan thought this was odd. So many years ago, a long time before starting Koho - a company now worth over $250M- Dan started working with performance coaches. In this episode, he walks us through how to pick a coach, wh…

Ask most early-stage founders what they need most and you'll likely get the same answer: money. Especially early on, before you have much traction, raising money can be daunting. If you don't have much of a network, it's hard to even know where to start. Who are these angel investors and how do you…

Launching a marketplace is hard. The chicken-and-egg problem often seems insurmountable. In 2021, Wattpad was acquired for over $600M. But it wasn't easy. Early on, Wattpad cofounder and CEO Allen Lau almost gave up. He discu...