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Wil Schroter and I talk about my burnout

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Oct 13, 2021
I almost cancelled today’s interview with Wil Schroter because on the way to the office I was feeling all the weight of burnout. So instead of talking about Startups.com, the company will built, I’m going to talk to him about this.

Bringing technology to the parking industry

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Oct 11, 2021
Jerry Skillett is the founder of SPACES, a contactless parking payments platform.

The software taking the teeth out of manipulative marketing

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Oct 7, 2021
As someone who loves whiskey, I know that most purchase decisions come down to marketing and how the bottle looks. Well, today’s guest noticed that too–particularly in the wine industry. So she created a solution to demystify taste and help consumers make better choices based on...

Solving the customer testimonial problem

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Oct 4, 2021
Testimonials are a thing that a lot of businesses are looking for. The problem is that most of them are boring, unclear, and unconvincing. Today’s guest is trying to fix that. Sam Shepler is the founder of Testimonial Hero, a B2B customer video company with both on-site videography (zero...

Productizing personalized growth

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Oct 1, 2021
Today’s guest is solving a problem that I totally understand. But it’s not an easy problem to address at scale. I want to find out how he’s doing it. Omer Glass is the founder of GrowthSpace, which creates personalized growth programs for your employees. I invited him here to...

Buying and selling online businesses

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Sep 29, 2021
Joining me is someone who told me this idea they had about buying, building, and selling multiple underdeveloped content side. At the time, I wasn’t sure it was a good idea because it felt like spreading spreading oneself too thin. Turns out I was wrong. Rohit Gandrakota is the founder...

The simplest $6M dollar idea

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Sep 27, 2021
Today’s guest is doing $6M ARR selling freaking air fresheners. Seriously, just a better replacement for those little trees that hang from the rearview mirror. He says selling a fragrance over the internet is the world’s worse elevator pitch but I disagree. I want to find out how he...

Building a global business from a small market

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Sep 24, 2021
Rahul Aggarwal is the founder of Desighill, a creative marketplace for businesses and individuals. He built it and is running it from India even through only a small percentage of their customer base is represented there. I want to find out how he’s doing it.

What I’ve learned from 2,000+ interviews

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Sep 22, 2021
I haven’t talked about this much but I have a new book coming out in October. The book is full of conversation techniques I’ve learned after 14 years and 2,000 interviews. The book is called Stop Asking Questions. I was interviewed by Tom Boyd of the Creators Are Brands podcast about...

Why there’s still room in the productivity space

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Sep 20, 2021
Alice Default is the co-founder of Double, which connects busy executives with experienced part-time assistants and delegation tools. I want to find out why she went from building software to building a service company.

Reinventing a business killed by COVID

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Sep 17, 2021
Joining me today is an entrepreneur who had a business that suffered of COVID closures in the restaurant space. So he rebounded with an idea that I think most people expected to fail. I want to find out why he hasn’t. Vitaly Alexandrov is the founder of Food Rocket, super-fast, on-demand...

Finding a gap to fill in online education

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Sep 15, 2021
Joining me as an entrepreneur who took on the cloud at a time when people were not as enthused about it as I would have expected them to be. And so he looked around and realized that there’s a world of parents who want to teach their kids English but they lack access. So he created an...

The profitable business model you’ve never heard of

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Sep 13, 2021
I can’t believe that today’s founder created a company that’s in my world, in my space, and I didn’t know it existed. It’s a fantastically successful company with a model that just makes sense. How did I not know that it existed and how could so many of these...

The startup powering your streaming videos

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Sep 10, 2021
Today’s guest figured out that distributing streaming video is becoming more complicate, not less complicated. So he created a way to make it easier for developers. Jon Dahl is the founder of Mux, an API that enables developers to build unique live and on-demand video experiences.

Outsourcing the role of technical co-founder

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Sep 8, 2021
One of the things that new entrepreneurs keep looking for is how to get a technical co-founder. They have an idea but they need somebody to partner with to actually build it. Well, joining me is someone who essentially is a technical co-founder you can hire. Chris Stegner is the founder of Very...

The liquor alternative making $10M ARR in 2 years

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Sep 3, 2021
My guest today is someone who came up with a counter-intuitive product that I think a lot of people in my audience can probably really relate to. There comes a point in your life when you’ve got kids, you’re running a business, you’ve got to get up early, and so you...

How to outsource your tax headaches

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Sep 1, 2021
Scott McFarlane is the founder Avalara, tax compliance software.

How Early (Repeated) Mistakes Gave Birth to a $1MM Creative Solution by Solving His Own Problem

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Aug 30, 2021
Joining me is someone I’ve known for years and watched as he struggled with challenges with his business. But I also saw how committed he was. He’s here to talk about what that was like and how he pulled himself out of the hardest moments. Matt Ackerson is the founder of...

Turning a physical product into a service

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Aug 27, 2021
Today I’m talking to two cofounder about this unbelievable service they have created. It’s a fascinating model solving a very specific pain point for a very specific group of people. I’ll ask them about it all in this interview. Erik Rico and Oscar Llarena are the founder of...

Bootstrapping an ambitious idea in crypto

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Aug 25, 2021
Today’s guest is solving such a pain for anyone who has ever tried to make a transaction using cryptocurrency. I would have guessed that he was backed by huge VCs based on the product he’s built but it turns out the whole thing is bootstrapped! I want to find out how he did it....

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