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How to recover from a cashflow crisis without mortgaging your home

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Apr 14, 2017
Nathan Barry is back and I’m going to be honest about why. Awhile back Nathan was in a situation where he needed money to keep his company going. He was even considering mortgaging his house. Since then he’s built up his company on such sturdy ground and I have to find out how he did it....

The model for building a business on social media

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Mar 10, 2017
I don’t think in 1000+ interviews I’ve seen someone use social media as well as today’s guests. These guys built up their business using influencers. That’s what they’re good at and it’s how they bootstrapped their business. I invited them here to talk about how they did it. Nik...

How Nick Gray created a $1M business by hacking museum tours

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Feb 24, 2017
I hate to admit it, but I hesitated when someone suggested today’s guest. And you’ll see why when I tell you what he does. Today’s guest is Nick Gray. He is the founder of Museum Hack, which encourages people to explore museums in a new way. I get how that would be fun but I wasn’t sure...

How TickPick is bootstrapping against competitors like StubHub

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Feb 6, 2017
What excites me about this guest is that he’s heard me interview two of his competitors. He knew going into his space that there were tons of competitors—so why did go into it? And how is he still standing? Brett Goldberg is the founder of TickPick which offers a no-fee ticket marketplace...

How a jerky founder learned to lead with emotional intelligence

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Jan 16, 2017
Today’s guest says that at one point in his life, he was a real ass. He says he was pushy and insistent on his approach until he discovered a better way. I initially invited him here just to talk about his business but I had no idea he’d be open to talking about that and the issues he had...

How Groove built a better mousetrap in helpdesk software

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Jan 4, 2017
Today’s guest does not do a lot of interviews like this. This might be the first one he’s ever done, and I’m proud to have him on here to talk about how he built up his company. How did he do it? It started with blogging about his journey and talking about his company and how...

How to land partnerships with big national brands

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Dec 19, 2016
Today’s guest had a problem. He wanted to give a card. He wanted to pay for a friend’s dinner remotely. He couldn’t do it and said, “I think there’s a solution here. I think I can build it.” And he built it up and my team of researchers talked to him. We...

How Chip Baker got into the business of marijuana

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Dec 12, 2016
Before I tell you about today’s guest, I want to tell you that I was watching the election results and saw that marijuana was legalized in California. I didn’t sit back and say, “Great, now I can smoke.” I said, “Great. I wonder who is building a business that is going to profit from...

Behind-the-scenes SEO and backlink strategies

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Dec 2, 2016
I’ve got an entrepreneur here who–man, this guy’s had so many ups and downs. He worked on this business for so long that he physically experienced pain, all kinds of issues with his body, with his hands, with everything because he was trying to build this business up. I love...

How an accidental entrepreneur built and sold coding school DevMountain for $20,000,000

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Nov 16, 2016
In the years that I’ve been doing these interviews, I’ve done a few with entrepreneurs who have built coding schools. At first it took me by surprise. How can a school do really, really well? That’s similar to the interview we have today but the twist is that today’s guest is really...

Pattern for creating a profitable startup?

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Nov 7, 2016
Dane Maxwell is a founder of Paperless Pipeline, software that simplifies real estate transaction management and of The foundation, which can help you start a software business even if you have no experience.

How Drip started as a widget and was acquired by Leadpages for a life-changing sum

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Nov 2, 2016
I’m really excited to have today’s guest on. This is a guy who has started things like MicroConf and Micropreneur Academy and he’s just been plugging away, bootstrapping from his house. The stuff he creates is high quality, the people he works with love him and have life-changing...

Former SuperStats co-founder on his $30M daily deals site

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Oct 17, 2016
Today’s guest has been running a company that’s really big but I’d never heard of it. Once I did hear about I couldn’t stop looking into it. Today’s guest is Jeremy Young, founder of Tanga, which is an online deals site. For me, if the deal site includes electronics I just get...

How a husband and wife turned proofreading into million dollar idea

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Sep 23, 2016
My focus is tech and software entrepreneurs who have big revenues or big exits. Today I’ve got an entrepreneur who’s not exactly tech, but I read about her story in a Business Insider article that was published about a year ago, how she and her husband were traveling through South...

How a hippie raised in the woods of Maine coded (and sold) Infoactive

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Sep 2, 2016
Joining me today is an entrepreneur who really did not have a tech background. She had a hippie background that I’m so excited to talk about. But what’s even more interesting is the thing that she did to get into tech world and the startup world. It was something that shows what she’s...

How to use community to grow a physical product (even in a crowded market)

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Aug 10, 2016
Because I do these interviews I get invited to speak at conferences. Well, a few months ago I was at a speaker dinner for a conference and the organizer said to me, “Andrew, you’ve got to come meet this woman. She just launched this bag company.” Bag company? What’s so exciting about...

How a techie dad built SellHack (while battling a life-changing diagnosis)

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Jul 18, 2016
We’ve got with us Ryan O’Donnell. He’s a guy who says that he and his cofounder are two techie dads who prefer to spend a coffee break in the middle of the day with their kids than with coworkers. They want to build the kind of company that they enjoy working in and that...

How Mitchell Harper built a $100,000,000 company, failed, and got back up

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Jun 22, 2016
I hope that decades from now people go back to these interviews to learn from this crop of entrepreneurs. And one I’ll be most proud is my interview with Mitchell Harper of BigCommerce. He’s a guy who started out bootstrapping, who built an incredible company, and who came on to talk about...

DesignCrowd founder doesn’t do interviews (except for this one)

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Jun 20, 2016
A few months ago we had a sponsor named DesignCrowd that I talked about a couple of times in interviews. But in private, my team and I were saying, “Those guys are making bank.” But we couldn’t really figure out how big they were. The more we looked into it, the more impressed...

How Robin Smith turned an offline headache into the online platform WeGoLook

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Jun 17, 2016
I’ve got someone whose story who you’ve probably never seen on major media, but you should because it’s exciting and inspiring. Today’s guest grew up on a farm. To me, having grown up in New York, it feels like the middle of nowhere, and she had a bunch of setbacks which...

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