From Solo Developer to Venture Scale Entrepreneur: Jordan Boesch, CEO of 7Shifts (Part 1)

Jordan started as a solo entrepreneur in a small province of Canada, Saskatchewan, and has built a heavily funded, high-growth SaaS business. Fascinating journey!

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

Jordan Boesch: I’m from Saskatchewan, a province in Canada. I’m the CEO at 7Shifts which is a team management platform. Before 7Shifts, I was a software developer for many years. I ended up working for my dad who ran some Quiznos locations.

Bootstrap First, Raise Money Later and Build a World-Class AI Startup from India: Raghu Ravinutala, CEO of Yellow.ai (Part 2)

Sramana Mitra: You got to a million ARR on the strength of those first 10 customers?

Raghu Ravinutala: No, once we got the 10, we got more. When we were at $1 million, we had 35 to 40 customers.

Sramana Mitra: You didn’t have to raise money until that point?

Raghu Ravinutala: Correct.

Sramana Mitra: How many people were you then?

Bootstrap First, Raise Money Later and Build a World-Class AI Startup from India: Raghu Ravinutala, CEO of Yellow.ai (Part 1)

Raghu has built an incredible AI startup from India with a global base of enterprise clients. Fabulous story!

Sramana Mitra: Let’s start by introducing our audience to yourself as well as the genesis of Yellow.ai.

Raghu Ravinutala: I’m the Co-Founder and CEO of Yellow.ai. Yellow.ai enables enterprises to drive automation on their customer experiences and employee experience by integrating a whole set of enterprise data and delivering phenomenal experiences that the companies can leverage for sales, marketing, HR, and IT automation.

Bootstrapping an E-Commerce Startup with a Paycheck to Exit: Jay Perkins, Co-founder of Kettlebell Kings (Part 5)

Sramana Mitra: You sold from bootstrapped directly to exit right?

Jay Perkins: Right. When you’re building a business, it’s not easy. You can live and die with the day-to-day. Something good happens and you’re on cloud nine. Then a customer gets a damaged product.

Sramana Mitra: What kind of exit price did you get for your business?

Jay Perkins: I’m not sure if I’m comfortable sharing.

Bootstrapping an E-Commerce Startup with a Paycheck to Exit: Jay Perkins, Co-founder of Kettlebell Kings (Part 4)

Sramana Mitra: How long from the point you started did it take you to get to $1 million? How long did it take you to get to $5 million?

Jay Perkins: A million would have been in our fourth year. We did $60,000 in our first year, $270,000 in our second year, and $750,000 the next year. Then $1.5 million in the fourth year. We probably could have gotten there sooner, but we were hindered by the things I mentioned. It was into our 7th or 8th year that we got to $5.5 million.

Sramana Mitra: What year was that when you reached $5 million?

Bootstrapping an E-Commerce Startup with a Paycheck to Exit: Jay Perkins, Co-founder of Kettlebell Kings (Part 3)

Sramana Mitra: At what point did you plug Kabbage into your financing process?

Jay Perkins: That was probably about four or five years in.

Sramana Mitra: So for four years, you operated as a fully-bootstrapped company?

Jay Perkins: Yes, it was tough. We’d be out of the most popular SKUs for four to five months at a time. One, we didn’t have any historical data for projecting them. Two, we were growing. What data we did have doesn’t necessarily apply to the future. It took a while for us to even out that process.

Bootstrapping an E-Commerce Startup with a Paycheck to Exit: Jay Perkins, Co-founder of Kettlebell Kings (Part 2)

Sramana Mitra: What did you do? You said you started a company on the BigCommerce platform?

Jay Perkins: I started a business called Kettlebell Kings while I was still employed at BigCommerce. Kettlebells are basically fitness equipment. Along with my co-founders, we would hold meetings for a year and a half leading up to when we formally launched. We knew we wanted to start a business.

We were like-minded, but we didn’t know what we wanted to sell. We would kick around ideas. We eventually decided on kettlebells. There just weren’t a lot of companies focused on building a product and lifestyle brand. We just went for it.

Bootstrapping an E-Commerce Startup with a Paycheck to Exit: Jay Perkins, Co-founder of Kettlebell Kings (Part 1)

There are roll-ups of e-commerce brands going on right now. This case study delves into one such that has exited into a roll-up effort.

Jay Perkins currently runs Living.Fit which produces digital workouts, fitness education courses, and fitness equipment.

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