Best of Bootstrapping: Bootstrap to Exit and THEN do a VC-Funded Venture

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

A very effective way to dance the entrepreneurial Waltz is to do a bootstrapped company first, sell it, and then do another venture with a more ambitious agenda. Jeremy Swift’s journey as Co-founder and CEO of Cordial is a great case study in this method.

Sramana Mitra: Let’s go to the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Jeremy Swift: I was born in Beaverton, Oregon. Most people know about Beaverton because of Nike. It’s a small suburb outside of Portland. I grew up in what I would consider a small middle class family. Both my parents were a rare breed and especially different from the path that I’ve taken in my life. The first job they got out of college is the same job that they retired with 40 plus years later.

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Best of Bootstrapping: Bootstrapping an AI Startup Using Services

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

Co-founder Nitesh Chawla bootstrapped Aunalytics while keeping his academic job at Notre Dame.

Sramana Mitra: Let’s start at the very beginning of your story. Where are you from? Where you born, raised, and in what kind of background?

Nitesh Chawla: I’m from New Delhi although I was born in Calcutta. I did my schooling from Delhi Public School. Then I did my engineering from Pune. Then I came to the United States in 1993 right after finishing my undergrad. I went to grad school in South Florida. I got my PhD in Computer Science with a focus on Machine Learning and Data Science.

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Best of Bootstrapping: SearchStax Founder Bootstraps to $10M Using Services

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

Founder Sameer Maggon discusses bootstrapping SearchStax to $10 million using services. Excellently navigated journey!

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, and in what kind of background?

Sameer Maggon: I grew up in Delhi. I did my engineering in Computer Science from Pune. Then I came back to my hometown to work for a document management company. Then I decided to learn more. I came to USC in Los Angeles and did my Masters in Computer Science. Since then, I’ve been in LA and worked in a variety of startups and larger companies in the greater Los Angeles area. 

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Bootstrap First, Raise Money Later: Art.com CEO Josh Chodniewicz (Part 6)

Sramana Mitra: Getting companies fundable is a high-touch process. That is not necessarily a scalable process. I would say we may be the only accelerator in the world that has done some scalability on that. We have created a lot of curriculum. We’ve done so many now. It’s like pattern matching. That takes time.

One of the things that we’ve done is we’ve released a large chunk of our curriculum on Udemy. Udemy has 50 million users. My point is, if you take on the job of trying to coach these people, that is very difficult. Then comes the issue of leading the round or just following.

Bootstrap First, Raise Money Later: Art.com CEO Josh Chodniewicz (Part 5)

Sramana Mitra: What did you do after Art.com?

Josh Chodniewicz: We were in San Francisco. I moved to New York and lived a couple of years there. Frankly, I think I dealt with an identity crisis. All I knew was Art.com. I had to get around that. I started making investments in startups. I saw quite a bit of success in that.

Sramana Mitra: What did you invest in that really did well?

Bootstrap First, Raise Money Later: Art.com CEO Josh Chodniewicz (Part 4)

Sramana Mitra: We are now in 2004?

Josh Chodniewicz: 2001 was when we acquired Art.com. Then 2004 was when we raised $30 million and combined it with our leading competitor at that time called AllPosters. I called up the other CEO and said, “We can shoot bullets at each other or we can join and shoot them at the rest of the world.” We put the businesses together in 2005.

Sramana Mitra: You ran the company?

Bootstrap First, Raise Money Later: Art.com CEO Josh Chodniewicz (Part 3)

Sramana Mitra: What was the revenue trajectory with search engine and affiliate marketing as the drivers?

Josh Chodniewicz: The other consumer driver for us was our partnership with eBay in 1998 to list our products. We were talking to eBay about why their marketplace didn’t have the traction. The problem was their listing fee. They were charging a 10-cent listing fee.

Bootstrap First, Raise Money Later: Art.com CEO Josh Chodniewicz (Part 2)

Sramana Mitra: Why Art.com?

Josh Chodniewicz: This was in 1994. It was a while ago. A buddy of mine called me up. He was at Virginia Tech. He was getting his Computer Science degree there. He said, “Josh, I know something that’s going to be huge one day – the internet.” We started talking about it.

I bought myself a modem and started playing around with it. We brainstormed in a diner in New Jersey. Nobody was using it. To give context, one out of 800 Americans had an email address in 1994.