From Solo Developer to Venture Scale Entrepreneur: Jordan Boesch, CEO of 7shifts (Part 2)

Sramana Mitra: Beyond your dad, how did other customers find you?

Jordan Boesch: We had it online and people were finding us because they were just looking for scheduling software. They would google us and they’d sign up. I didn’t think anything about how to expand and get more. It was really just a fun project for me where folks could sign up and I could talk to them and learn about their needs. That’s how people found us.

Sramana Mitra: How much were they paying?

Bootstrap First, Raise Money Later and Build a World-Class AI Startup from India: Raghu Ravinutala, CEO of Yellow.ai (Part 3)

Sramana Mitra: What are the numbers on Series B and Series C?

Raghu Ravinutala: In series B, we raised about $20 million. In Series C, we raised about $79 million.

Sramana Mitra: That’s a lot of money that you’ve raised. You’d have to build a huge company to return that investment. One of the things I’m hearing from a lot of enterprise startups that sell to the enterprises is that it has become easier to sell to the international market because buyers have become used to evaluating and buying online. Are you experiencing that as well?

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.