Bootstrapping to $23 Million: Michael Nemeroff, CEO of RushOrderTees (Part 2)

Sramana Mitra: Who was making these t-shirts?

Michael Nemeroff: They had a friend in the industry who did the printing for them. It wasn’t a partnership. It was like, “I have my own business. Do you want to start your own?” They went to the same guy to do the printing.

Sramana Mitra: You decided that this needs to go online and take orders online?

Michael Nemeroff: Yes. There was no automation. There was no e-commerce. It was just a website. It had blinking images and was a very old school website. The biggest thing was I made a big investment in advertising. Luckily, we closed a big tech school. They placed a big order with use and that allowed us to >>>

Morphing a B-to-C Idea to a B-to-B Business: Andrew Witkin, CEO of StickerYou (Part 1)

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

Andrew started with a B-to-C idea but has built a business that is primarily B-to-B from a revenue standpoint. Learn more about the nuances.

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?

Andrew Witkin: I was born in Toronto, Canada. My mom was a German immigrant and my dad was a Canadian citizen who happens to be Jewish. I grew up in a pretty loving family. I went through school and then decided to enter into an undergraduate business program because I was most intrigued with business. I went out to a school in eastern Canada.

In my final year, I actually went to the US and attended a US school. I was in Providence, Rhode Island in my final year. I found the pulse of >>>

Bootstrapping to $23 Million: Michael Nemeroff, CEO of RushOrderTees (Part 1)

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

From setting up a printing machine in the dining room to $23 million in revenue, Mike’s RushOrderTees journey is one of steady, diligent execution.

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

Michael Nemeroff: I was born and raised right outside Philadelphia. That’s where I’ve lived my whole life. It all started in high school. My parents were entrepreneurs. They owned a clothing line. It’s a lot different from what we do today.

Sramana Mitra: Having an entrepreneurial family is a very big driver in a lot of people becoming entrepreneurs because you grow up in >>>

Scaling a SaaS Business to 11,000 Customers: Booker.com CEO Josh McCarter (Part 6)

Sramana Mitra: What are some of the inflection points in the business when things started clicking in gear? We’ve talked about one of the key issues which is really turning into this metrics-driven organization. What other inflection points have you experienced in building this business?

Josh McCarter: I think there are a few. The early stage was just pulling the company out of the original parent company because that gave us the opportunity to go out and create our own business, our own P&L, and the ability to raise capital by ourselves. Being able to go out and start generating our early sales was very important.

Sramana Mitra: I’m asking a very specific question. It’s about an inflection point about customer adoption. As you trace the graph of >>>

Scaling a SaaS Business to 11,000 Customers: Booker.com CEO Josh McCarter (Part 5)

Sramana Mitra: What is your conclusion about where you wanted to pin your customer acquisition cost? How does that correlate to your lifetime value for your SaaS business?

Josh McCarter: All of the benchmark studies say that you need to be north of three times LTV. That seems to be the number where people feel like you’ve got your acquisition cost in line. Obviously, when you’re in enterprise sales, your months-to-payback are sub-12 months. When you’re in SMB SaaS, they’re usually sub-20 months. One of the things that we’ve really focused on is how to change some of our go-to market strategies so that we are less reliant on direct sales and more reliant on channel partners. >>>

Scaling a SaaS Business to 11,000 Customers: Booker.com CEO Josh McCarter (Part 4)

Sramana Mitra: What happened after you raised the $15 million? How did the business move? What were the strategic moves that you made to get to the next level?

Josh McCarter: The major move that we made was, we started investing in sales and marketing. We started building out our team. We took on some larger contracts that, in hindsight, were not the best things for us to do over the long-term for the company. They were big contracts. They were big name companies that helped us gain credibility with our investors and with other people in different segments. They were all multi-million dollar, multi-year contracts.

Sramana Mitra: What was wrong with those contracts? Typically, multi-million multi-year contracts are good news. Why was it bad news? >>>

Scaling a SaaS Business to 11,000 Customers: Booker.com CEO Josh McCarter (Part 3)

Sramana Mitra: What did you have in place when you went to raise capital?

Josh McCarter: We had a functioning framework of the software. We had about 700 customers and a team of about 30 people. It was, at least, beyond a prototype and proof of concept. The business was doing under $1 million in revenue. We had a good reputation and had some big marquee contracts with Hilton and some other hospitality brands.

We leveraged that saying, “This is real. There are transactions happening through the system. We want to extend it to other feature sets to help these businesses run.” Salons started signing up. We thought we could make a dedicated product for salons so we started pushing out in that direction. We ended up building out the business from there. >>>

Scaling a SaaS Business to 11,000 Customers: Booker.com CEO Josh McCarter (Part 2)

Sramana Mitra: What year does this bring us up to?

Josh McCarter: Around 2001.

Sramana Mitra: What happened then?

Josh McCarter: The company’s IPO was successful. After six years, I was looking to do something new. I went and joined a company called Spafinder. It was a travel-based magazine and was call center-oriented. We were trying to turn it into an online travel content company. We ended up joining with that team and worked on that business for a couple of years.

I ended up on the Board and decided to look up a few other business models. I connected with some friends in business school at USC. One of them had >>>