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Building two companies in the same space

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Mar 21, 2022
The thing that I’m especially curious about today’s guest is that his current business is very similar to his previous business. Why is it that more entrepreneurs don’t do that? Anthony Welgemoed is the co-founder of Ziflow, creative collaboration and proofing software....

An update on Ukraine from Aleksandr Volodarsky

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Mar 17, 2022
I’m kind of sad about this interview because joining me is someone who I’ve watched in the startup community for a long time, who I’ve become friends with. He’s been in Ukraine and I’ve watched him deal with what’s going on there. Aleksandr Volodarsky is the...

Web scraping as a business

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Mar 14, 2022
Today’s guest had been hearing about stories of entrepreneurship and finally he took the leap himself. And do you know what happened? He failed. Badly. You’ll hear that story in this interview and how he eventually got to where he is today. Kevin Sahin is the founder of ScrapingBee,...

GrubHub founder Mike Evans is starting over

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Mar 7, 2022
I first interview Mike Evans 12 years ago when he was hustling to get GrubHub off the ground. It’s mind-boggling how much he got done in those 12 years and I want to find out about all of it: the IPO, the exit, the time off, and the new start. Today, Mike Evans is the founder of Fixer, an...

Start a service business in minutes

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Feb 28, 2022
Today’s guest has been starting businesses since high school. But what’s interesting is that they were all in really different spaces. He ended up taking all that experience and launching his most recent company, Durable. James Clift is the founder of Durable, which makes owning a...

Turn a product from a nice-to-have to an essential

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Feb 21, 2022
Arvind Jain noticed a problem that so many founders running a remote team can relate to. Here’s the scenario: a person on your sales team wants to know what new features are in the product pipeline. They need the answer to close a sale, but the answer is buried in a Slack channel, or a...

Brutally honest Gen Z insights

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Feb 14, 2022
Today’s guest landed clients like Ebay, NFL and Pepsico all within a year of launching. He basically replaced the old school focus group model and turned into something more relevant and more scalable. I want to find out how he did it. Jay Richards is the founder of Imagen Insights, a...

Capsule is going after pharmacy giants

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Feb 7, 2022
Why is picking up a freaking prescription at Walgreens or CVS one of the worst experiences? Today’s guest asked himself that not too long ago. And what did he do? He found a new way. Eric Kinariwala is the founder of Capsule, the pharmacy that delivers prescriptions, the same day, for...

Launching a hardware company quickly

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Feb 3, 2022
I am fascinated by the business that today’s guest created. Eli Harris is the co-founder of R-Zero, which designs hospital-grade disinfection solutions for the day-to-day realities of modern businesses. I want to find out how he got a hardware business up and running so quickly in this space.

The story behind Artlist

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Jan 24, 2022
Today I’m talking to Ira Belsky, the founder of Artlist. Ira was a filmmaker and recognized a really painful problem with licensing and sourcing creative materials. I want to find out how he transitioned from filmmaker to bootstrapped entrepreneur. Artlist provides royalty-free music and...

Connecting content creators and brands

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Jan 21, 2022
Keren Sachs is the founder of The Luupe, a marketplace for brands to connect with and hire diverse photographers. She started as a photographer, but what made her different was she understood the business side of the industry. I’ll ask her about how she landed her first ever job at...

Solving the e-commerce problem for alcoholic beverage brands

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Jan 19, 2022
My guest today has found a way to solve a very frustrating problem: buying alcohol online. It’s frustrating for consumers who can order basically anything else with one click and it’s frustrating for creators who have to use old channels to sell their products. Adi Pal is the...

The upside of naivety when you have a big idea

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Jan 17, 2022
When I interviewed the founder of Tradeshift ten years ago, he had a very simple idea: Facebook for businesses. I don’t think even he could have imagined the complex problems he would encounter along the way. Things like global tax compliance, cloud security and enterprise integrations....

Bringing tech to hospitality

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Jan 14, 2022
I’ve been feeling the pain that today’s guest is out to solve. Since moving to Austin, my wife and I still haven’t found a place to buy. So we’ve been jumping from Airbnb to Airbnb and we’re going a little crazy. Well, Luca Zambello found a way to make those...

Using entrepreneurship to protest

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Jan 3, 2022
For years, I thought protesting was a waste of time. To me, the only thing that works is to actually come up with something better. So I’m really excited that today’s guest John Laster, somebody who had been out there protesting and finally said, “You know what? Why are we...

A conversation with Deron Triff of WaitWhat and TED

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Dec 22, 2021
I want to understand about the business of content creation so invited Deron Triff. Deron  is co-producer of the Masters of Scale podcast. And prior to that, he was on the executive team at TED. He is THE person to talk on this subject. Today Deron is co-founder WaitWhat, a New York based media...

How Netflix founder finds inspiring ideas

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Dec 20, 2021
My big goal for this interview is I want to find out how you decide what to do with your life? And I have the perfect guest to guide me through that question. Marc Randolf is the co-founder of Netflix–I want to talk to him about that–and why he’s now in podcasting. Today, Marc...

Songfinch is reinventing music making

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Dec 17, 2021
Songfinch today: Anyone can have a custom song written for their loved one, client, whoever. Nice business. Growing fast. The future: well, listen to the end. I think you’ll get why this is a much bigger idea.

AMA with employee one at DoorDash

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Dec 15, 2021
Today Andrew Munday is the founder of Local Kitchens, a micro food hall that lets you mix-and-match your favorite local restaurants in one easy order. He emailed me recently about how he was the first employee at DoorDash and all the things he could talk about from that experience. I’m so...

$1M in less than a year

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Dec 13, 2021
My guest today started a business in January 2021 and has already hit $1M in revenue. But that’s not even the most amazing part. What amazes me is that he did it in a space that I would have thought was too mature for that type of growth. So I invited him here to find out how he did...

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