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How a chain of gyms inspired a software company

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Jan 15, 2018
Today’s guest had a job and came across a problem that was so painful he decided to solve it. As a result, Mike Brown is the founder of FISION which is sales enablement and marketing asset management tool. It gives salespeople all the digital assets they need to close more sales. He went all...

Solving the problem of lifecycle engagement

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Jan 12, 2018
It’s not that hard to get downloads for your app. What is hard is to get people to remember to keep coming back and using your it. The retention is so hard. Today’s guest is an entrepreneur who understood that pain long before other app makers and digital brands understood it. He created a...

A food delivery lifestyle business pivots to solve a bigger problem for grocery stores

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Jan 8, 2018
About six years ago I interviewed the entrepreneur you’re about to meet. He started a snack delivery service called Madtown Munchies and he built it up from one guy with a bicycle to a $380k business. We stayed in touch after that interview but recently I’ve been wondering what happened to...

The business behind hosting companies

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Jan 5, 2018
Today’s guest is an entrepreneur who had a hosting company. They had a challenge with hosting videos on their site and they thought, “Let’s create a product that solves it.” And they did. And then it failed. But then they kept talking to their customers and understanding...

Building a company for legacy instead of exit

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Jan 1, 2018
Personally I think the importance on how fast a company can exit is the wrong way to think about business. More valuable than the exit is the legacy you leave behind and the impact your company has on the world. That’s why I’m so proud to have today’s guest on. He started back in the days...

How to systemize idea validation

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Dec 27, 2017
If you want to launch a new product but you want to figure out if it will even work before you launch it, today’s guest has found a way to help. Thor Ernstsson is the founder of Alpha which helps teams make better decisions based on users, products, and new markets. Here’s what that...

Case Study: How to get customer insights

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Dec 22, 2017
When I heard that the founders of LessAccounting sold their company I was completely surprised. They sold to another accounting software company that I’d never even heard of. Well, today I have founder of that company. Uday Koorella is the founder of Qount, which provides accounting...

How to turn your consultancy into a SaaS

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Dec 15, 2017
You know from these interviews that founders who address a deep pain for their customers are the ones who create the most dependable successes. Today’s guest was doing consulting work when he and his team uncovered an issue that his clients had. Well, that issue lead him to create a software...

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...

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