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Nobody thought the old game of chess could turn into a real business in a world with internet. Frankly, there was a time when Erik Allebest, Chess.com’s founder, didn’t think it would and even tried turning his attention to a bigger, sexier market. But through constant cranking...

Today I’m talking to Kara Goldin, the founder of Hint, a flavored water I see all over San Francisco. I invited her here to talk about how she built up the business and a large part of this interview is based on her freaking amazing book, Undaunted: Overcoming Doubts and Doubters. I...

If you’re an entrepreneur who had an idea for a physical product but is overwhelmed by the idea of bringing it to life, you need this interview. John McEleney is the founder of OnShape, a Software-as-a-Service product development platform.

My guest today is someone who comes off humble but I’m here to challenge him on that. I think it’s an act. We’ll find out in this interview. Andrew Gazdecki is the founder of MicroAcquire which lists startups with $500,000 ARR or less.

Today’s guest was not the type of person who was selling candy as a kid because he was so entrepreneurial. But he did really care about health–particularly mental health. So Steve Lee and his brother built a mindfulness app called Aura. In this interview, we’ll talk about how...

Today’s guest created a car wash company that I am so freaking fascinated by. He took an old business model and was able to incorporate a membership component to it. Well, that business led to an experiment that gave him an entirely new business idea. I want to find out how he did it....

My guest today couldn’t understand why the research industry wasn’t catching up to the technology of, say, the advertising industry. So he decided to do something about it. Patrick Comer is the founder of Luc.id, which helps companies make data-driven decisions inspired by the...

Today’s guest is someone who got $250K in credit card debt while trying to build his first business. In this interview, you’ll hear how his stubbornness got him out of that situation and into back-to-back multi-million dollar e-commerce businesses. Today, Jeff Lee is the founder of...

Today’s guest is someone who was new the US but had a great job and was making good money. So imagine how surprised and embarrassed he was when he was turned down for a Costco credit card when shopping with his family. That experience led him to look deeper into the market and see that...

It’s been said that the best businesses ideas are just replacements for spreadsheets. Well, that’s what today’s guest figured out after the failure of his first business. Raj Sheth is the founder of Recruiterbox, applicant tracking software. I’ll find out how he did it in...

One of the popular dinner topics here in San Francisco is who invested in what. And it’s one of those things that can easily feel exclusive because you have to spend time to build relationships, you have to have access, you have to have opportunity. And that’s where today’s...

My guest today told his customers he didn’t love the business. They were shocked. Admitting it wasn’t working allowed him to create a new business. Today Chris Brisson is the founder of Salesmsg, simple, scalable, two-way business texting.

Joining me is someone whose business failed so many times that most people would started over with something new. He didn’t. And today the business is worth $1.4 billion. Beerud Sheth is the founder of Gupshup, a smart messaging platform that enables developers to build messaging services...

When Ryan Hoover suggested that I meet today’s guest, I knew it was going to be an interesting person. And when I looked into the company that today’s guest created, I wanted to be a customer as quickly as possible. Dylan Beynon is the founder of Mindbloom, a platform that provides...

Before talking to today’s guest, I would have guessed that the craft beer market was fully saturated. In this interview, I’ll find out why he thought there was room for one more. Josh Landan is the founder of Saint Archer, a craft brewery that was sold in 2015. I also want to ask him...

I remember when I first saw the software that today’s guest created. The fricking name got my attention immediately. Tyler King is the founder of Less Annoying CRM, a simple CRM built just for small businesses. The name itself acknowledges and communicates the pain that he’s solving....

Joining me is an entrepreneur who discovered how effective LinkedIn is for building relationships, but also for marketing and growing sales. So he created a tool that will allow you to do that. In this interview, we’ll talk about specific growth hacks and the challenges of the...

Joining me is someone who built a business off of writing and then realized, you know, the bigger this business gets, the less happy I am. Nicholas Cole is the co-founder of Digital Press, a thought leadership agency for CEOs, executives, and serial entrepreneurs. In this interview, I’ll...

I’ve got to be honest, I’m not as interested in the software today’s guest created as I am in his story. Dave Chesson started out as a nuclear engineer and arms dealer. He began writing books while out at sea. When he left the military, he turned that experience into a side...

You ever feel like you just know what’s going to happen? You know the future of Bitcoin or you know who’s going to win the game? Well today’s guest found a way for people to actually get paid for their predictions instead of just ranting on Twitter. John Vitti is the founder...