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GroupMe founder on his $80M exit (and why he’s building his new company differently)

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Dec 6, 2017
I’m so excited about today’s guest. Years ago he created a software that allowed a group of people to talk to one another over text. It was called GroupMe and it felt like as soon as I even heard about the company it was sold in a life-changing exit. I always admired how they did it....

How to look at the data behind your startup

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Dec 4, 2017
My hesitation for you about this interview is once you find out what today’s guest does, you’re kind of going to feel a little bit like my mom did the first time I took her to an Apple Store. She was completely intimidated by the technology. Sometimes the things we’re a little...

Case Study: Bringing a bootstrapped European software to the U.S. market

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Nov 29, 2017
Accounting software is just a pain in the butt. As much as they modernize it, it still feels centuries old much more complicated than it needs to be. Well, today’s guest said, “I’m a simplifier. I’m going to jump in and create new software that will actually make it...

How a salesperson turned founder (by solving a pain for other salespeople)

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Nov 24, 2017
Today’s guest was a salesperson who was working in the field–he was driving around, talking to customers. And he noticed a pain. He was having trouble finding out where people were, how to get to the right people at the right time, and said, “You know what? There ought to be a...

How do you scale company culture?

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Nov 6, 2017
Today I have Jeff Epstein, the founder of Ambassador, who I interviewed about four years ago. Since I last had him on Ambassador has grown 5x. I want to find out how he’s grown and scaled his team. I want to spend a lot of time talking about company culture for a business that has grown so...

Magento founder Yoav Kutner on open-source products

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Nov 3, 2017
Today’s guest and his team created Mageneto, a commerce software so many of my guests say they used to build their sites. They sold to eBay and Yoav, who’s here today, wrote a nasty post about eBay which he later removed. I want to find out about that. I also want to find out how he went...

How childhood homelessness and the military made Jake Hare a better founder

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Oct 30, 2017
There are a few things that make today’s guest unique. He’s an entrepreneur building a consulting agency catering to unfunded startups. He was also homeless at one point and I want to find out how that influenced how he thinks about money and business. Lastly, I want to know how he...

How William Moore built a company so good Ross Perot wanted to buy it

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Oct 27, 2017
Today’s guest created a company and sold it to Ross Perot—Ross Perot! It’s called Rothwell International. It’s a contract programming company focused on object technology and, of course, we’re going to talk a little bit about the company that he’s got now. William...

How do you explain a hard-to-explain business?

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Oct 23, 2017
I pride myself on researching my guests—but I couldn’t research today’s guest enough. Every time I dug down to understand what he does I still felt I didn’t understand. Apparently if you pay him enough, he and his team of geniuses can solve just about any problem. Walter O’Brien is...

Born in Belarus, now building software in San Francisco

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Oct 20, 2017
Today’s guest used to sell berries and now he sells software. Mikita Mikado is the founder of Pandadoc, an all-in-one solution to automate your contracts, proposals, quotes and more. I invited him here to talk about how he started and grew his business.

How Bonus.ly is helping companies show recognition to employees

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Oct 18, 2017
Today’s guest helps entrepreneurs like me stop being ungrateful. Raphael Crawford Marks is the cofounder of Bonus.ly, a platform for employee recognition via a peer-to-peer microbonuses and rewards. I invited him here to talk about how I can improve in recognizing my team and how he built up...

Chat bots: How to get clients

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Oct 13, 2017
I’m so freaking obsessed with chat bots because I think it’s the future of online engagement. We’re spending more time in chat apps than we are in email and even social media. The guest I have for you today was running a successful businesses but he too became so obsessed with chat bots...

How a guy with no money launched a startup on Craigslist

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Sep 8, 2017
Imagine you’ve got no money, but you want to start a company. How would you do it? Well, today’s guest is a guy who was in that situation and decided he was going to start with nothing but a Craigslist ad. You’re about to hear how that took off. Michael Georgiou is the...

Case Study: Hiring a salesperson

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Aug 25, 2017
There’s a pattern that I noticed and I want to understand it a little bit better. The pattern is that successful entrepreneurs start out by understanding a specific customer pain, often by experiencing that pain themselves. Then they create a solution in the form of software that solves...

Can’t find a pain point? There’s another way to find your biz idea…

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Aug 18, 2017
I’ve noticed entrepreneurs will see a big problem in the world and they’ll create a business to address the pain point and capitalize on it. Today’s guest says he explicitly did not do that. He put down a list of criteria for what he wanted in a business and started thinking...

How to build a company using the psychology of incentives

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Aug 14, 2017
Imagine you are the CEO of a large Company and you have employees that need to travel everywhere. You want to make sure they get the lowest prices but you don’t want to micromanage them. So, how do you use psychology to incentivize them to find the best price? That’s what today’s guest...

How Master of Code is building chatbots for heavy-hitter clients

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Aug 11, 2017
I’ve been really obsessed with chatbots—I think it’s the future of company-to-human interaction. The more curious I got about the space the more I found out about the company Master of Code. At first I just thought of them as chatbot makers for heavy-hitter brands, but they do way more...

How Nowait modernized the restaurant waitlist (and sold to Yelp for $40M)

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Aug 2, 2017
I hate when I go to restaurants and I get one of those little plastic things that vibrates when my table is ready. I hate them because they don’t fit in my pocket, and I have to stand outside like a schmuck holding this thing in my hand. So when I heard that someone allowed restaurant...

Why sell a profitable company to take a risk on a new one?

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Jul 31, 2017
David Rogenmoser finally had a profitable business. PayFunnels, which allowed businesses to offer hassle free, fast, online payments. How did he do it? And, more strangely, why did he sell it take a risk on a new company, Proof? Proof allows you to boost your website conversions with intelligent...

How did Adii Pienaar launch Conversio and generate $2M in revenue in 2 years?

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Jul 28, 2017
What if you could build on your customer relationships simply by offering more attractive and functional email receipts? Adii Pienaar is the founder of Conversio which is an all-in-one marketing dashboard for eCommerce stores. Conversio helps eCommerce sites improve their relationships with...

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