Surviving Covid with a Bootstrapped Venture: Kristi Herold, CEO of JAM (Part 5)

Sramana Mitra: It also depends on what you are trying to accomplish because cash acquisitions are easy to rationalize on your balance sheet. If it’s an equity acquisition joint venture with another player, then that is not so easy to value. That is why I was probing that issue. Let’s go back to what happened when the pandemic strikes. How did you orchestrate and move forward?

Kristi Herold: As I said, we had two deals that we were doing our due diligence on that would have doubled the size of our organization by May or June of 2020. We had to put a pause on both of those. We were anticipating that we were going to be shut down for a month or two. I wasn’t anticipating that we would be here 13 months later not being to operate our sports league.

Surviving Covid with a Bootstrapped Venture: Kristi Herold, CEO of JAM (Part 4)

Sramana Mitra: What was your revenue in 2016 when you decided to switch gears?

Kristi Herold: We were doing $6.5 million in revenue. 

Sramana Mitra: That is substantial for a word-of-mouth business. 

Surviving Covid with a Bootstrapped Venture: Kristi Herold, CEO of JAM (Part 3)

Sramana Mitra: Give me the highlights of your strategy in growing this thing to that level. How long did it take you to achieve $1 million in revenue? 

Kristi Herold: It took me 8 years to get to $1 million in revenue. 

Sramana Mitra: In 1996, you started the business and then in 2004, you were up to $1 million in revenue?

Surviving Covid with a Bootstrapped Venture: Kristi Herold, CEO of JAM (Part 2)

Kristi Herold: I called everyone in my address book. I would also say, “If you know anyone that you think might be interested, will you send me their contact info?” I had friends faxing me their address books and then I would go through their address books and call everyone and tell them my idea. I kept doing that until I had about 800 names on my list.

I wanted to send out a paper newsletter. I couldn’t afford enough stamps for 800 newsletters. I could only afford 400. Luckily, my then boyfriend who was a pro-cyclist became my business partner and he ended up delivering 400 of those newsletters.

Surviving Covid with a Bootstrapped Venture: Kristi Herold, CEO of JAM (Part 1)

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

Kristi built a thriving bootstrapped business over twenty years until Covid hit. Read how she is surviving Covid.

Sramana Mitra: Let’s start at the beginning of your journey. Where are you from? Where were you born and raised? What kind of background did you have?

From Solo Entrepreneur to Serial Exits: Shane Neman, CEO of EZ Texting (Part 6)

Shane Neman: We had a real problem in finding affordable tech talent. I was in New York at this time. I bootstrapped it, so I was being very careful with how I was spending the money. In many ways that was an element of the success. It was my own money.

What happened was, we couldn’t find senior-level developers or DevOps people that we wanted. We started with trying to outsource to other countries. My senior developer at that time was from Ukraine. She was saying that she had two friends from college that were in Ukraine as well.

From Solo Entrepreneur to Serial Exits: Shane Neman, CEO of EZ Texting (Part 5)

Sramana Mitra: In 2007, JoonBug was sold, and you were fully into EZ Texting. Most of the proceeds from the sale have gone into EZ Texting, what happens next?

Shane Neman: I realized that I needed to quickly start scaling the business. I started hiring developers and salespeople. I went at it as a product-first company. I made sure that the product was so easy to use that any business owner could use it.

From Solo Entrepreneur to Serial Exits: Shane Neman, CEO of EZ Texting (Part 4)

Shane Neman: Back then, Shortcodes had just come out. Are you familiar with what Shortcode is?

Sramana Mitra: No. 

Shane Neman: It’s like those five or six-digit phone numbers that you text into to get a coupon. It’s a special five or six-digit phone number, and at that time they had just come out in the United States.