Navigating Multiple Product Pivots: Jebbit CEO Tom Coburn (Part 3)

Sramana Mitra: You were recruiting college students. When a brand wanted to do market research, they’d come to your site and you would not only provide them with software to run their surveys but also provide the focus groups.

Tom Coburn: Yes. When Dharmesh invested, we were a couple of thousand dollars in revenue. We probably had 50,000 students around the country. It was all US-based at that time. They were logging into our website. Half of our marketing team was focused on students.

Bootstrap First, Raise Money Later: Ben Hodson, CEO of JobNimbus (Part 2)

Ben Hodson: Later, that code ended up evolving into something that could auto-rekey those servers without ever having any downtime. We dubbed it Encryption Management. We hadn’t come up with all of that at the time when we were doing this business plan competition, but that was the seed of that idea. The business plan competition was really fun. You would go into a giant auditorium at the University of Washington. You would have a little booth. They gave a bunch of people Monopoly money that was given by business leaders in the area. These were people from well-known companies. I remember the CTO of Chase bank was there. High-level people from Microsoft were there. They would walk around and you would get to your elevator pitch.

Navigating Multiple Product Pivots: Jebbit CEO Tom Coburn (Part 2)

Sramana Mitra: Where did the $250,000 capital come from?

Tom Coburn: Our first investor was Dharmesh who’s the co-founder and CTO of HubSpot. 

Sramana Mitra: I just spoke with Dharmesh this morning. You met Dharmesh through Highland?

Tom Coburn: No. We’re very thankful to Dharmesh for being our first investor. That spurred a lot of other people to invest. Our story of meeting Dharmesh is very funny. I saw that there was a marketing conference in Boston. They were doing a mini Shark Tank competition. Dharmesh was one of the judges. He agreed to invest on just seeing the pitch.

Bootstrap First, Raise Money Later: Ben Hodson, CEO of JobNimbus (Part 1)

Ben is a serial entrepreneur with a long experience in bootstrapping and fundraising. Read on to see how he has navigated his journey.

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

Navigating Multiple Product Pivots: Jebbit CEO Tom Coburn (Part 1)

Tom discusses a very important aspect of building a product company: pivots.

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

Tom Coburn: I was born in a suburb outside of Boston, Massachusetts. It’s where the Boston Marathon starts. I grew up there and lived there all my life. I went to high school there at a local public high school. I ended up going to Boston College. I went there to study Biology and become a doctor. I ended up dropping out. I’d also picked up Theology as a double major. I was studying science and religion and ended up doing a marketing technology and data company instead.

Building HubSpot to a Unicorn: Dharmesh Shah’s Amazing Entrepreneurial Journey (Part 6)

Sramana Mitra: How many years did it take you through the $500 million to the IPO?

Dharmesh Shah: A little over seven years.

Sramana Mitra: This is basically what VC’s are looking for – to go from zero to $100 million in five to seven years. Not every entrepreneur has a venture that is amenable to that kind of timeline. This is hypergrowth. Hypergrowth is not a natural state of business. It’s rare and unique. If you don’t have a company that is going to go through hypergrowth, so what? Don’t get stuck on being venture capital friendly on your first venture, especially if you’re a first-time entrepreneur.

Building HubSpot to a Unicorn: Dharmesh Shah’s Amazing Entrepreneurial Journey (Part 5)

Sramana Mitra: It’s not a bad thing to have a tough time raising Series A. Most likely, you’re doing something new. The market is not crawling with 27 other competitors. The problem with that 27 competitors trying to raise money for the same idea is that it’s very noisy. A noisy market is very difficult to penetrate.

Dharmesh Shah: And very expensive. 

Sramana Mitra: What are the highlights of the HubSpot journey that you want to underscore and discuss?

Building HubSpot to a Unicorn: Dharmesh Shah’s Amazing Entrepreneurial Journey (Part 4)

Sramana Mitra: One question that comes to my mind is how many of those existing tools were you able to bring into your product design in version one? 

Dharmesh Shah: We did it from scratch. Our thinking was that we could have tried taking WordPress and Google Analytics and integrate them into this larger platform, but we wouldn’t be able to control the user experience in the way we needed. You have to control the boundaries and control the user experience in order to make it easy enough. We created everything.