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Bootstrapping Using Services: Sylvana Caridi Coche, CEO of Gravity Pro (Part 1)

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

Sylvana has an aura of no nonsense, no bullshit confidence about her that I find immensely attractive. Read her story to feel the force of sheer energy, smarts, and execution to learn how she did it!

Sramana Mitra: Let’s start by introducing our audience to yourself as well as Gravity Pro.

Sylvana Caridi Coche: I’m 42. I was born and raised in France. My parents were from Italy. They moved from Italy to France to find work because, at that time, it was hard for them because they were both illiterate. I was the last kid and grew up in a very low-class environment. I studied all the way to my doctorate, but I did not do my thesis because I went to work. >>>

Successful Pivot from B-to-C to B-to-B: Inkling CEO Matt MacInnis (Part 7)

Sramana Mitra: You said you’ve raised about $90 million. With all these changes and pivots, how has revenue in the new model tracked? Are you able to justify that kind of financing from a market cap point of view? I’m not talking about foo-foo market cap. I’m talking about market cap that is derived out of fundamentals.

Matt MacInnis: It has been punishing from an ownership perspective. Last year, the market was crazy. We did a small round at a really high multiple. This year, we did a bigger round. We did $25 million with Sapphire Ventures. That should take us to profitability. We gave up even more ownership. That part of it was tough. >>>

Bootstrapping With a Paycheck to Techstars: Nevin Shetty, CEO of Blueprint Registry (Part 7)

Sramana Mitra: How much investment did you get from Techstars?

Nevin Shetty: Techstars always puts in $100,000.

Sramana Mitra: How much equity did you give for that?

Nevin Shetty: Around 7%.

Sramana Mitra: You raised more money coming out of Techstars? >>>

Successful Pivot from B-to-C to B-to-B: Inkling CEO Matt MacInnis (Part 6)

Sramana Mitra: When you were starting to see this traction from Starbucks, KMPG, and other corporates, what kind of a business model did you follow in these deals?

Matt MacInnis: We knew it was going to be SaaS. We gave Starbucks a very sweet deal. They got extra for the platform for all their district managers on a one-year subscription agreement. The important set of things that happened at that moment in time was that we decided to go and recruit a VP of Sales. Keep in mind I had on staff a consumer marketer who was wrong for enterprise marketing. I had consumer engineers. You had to retool the whole company. It was really difficult to see that we were going to pivot from consumer. >>>

Bootstrapping With a Paycheck to Techstars: Nevin Shetty, CEO of Blueprint Registry (Part 6)

Sramana Mitra: The customer acquisition is Facebook primarily?

Nevin Shetty: It’s transitioning now to Pinterest. You have to think about where your users live. A lot of couples, who were recently engaged, go to Pinterest for inspiration for their wedding. As they’re looking for inspiration for their wedding, they see Blueprint there. Potentially, they come bock to Facebook or find us organically.

Sramana Mitra: So you’re advertising on Pinterest?

Nevin Shetty: Yes. >>>

Successful Pivot from B-to-C to B-to-B: Inkling CEO Matt MacInnis (Part 5)

Sramana Mitra: What kind of B2C traction were you experiencing at this point?

Matt MacInnis: Some titles performed very well. I should say that at some point in 2012, we also started doing non-academic content. Inkling is not an easy story to tell because we’ve adapted a lot.

Sramana Mitra: That’s okay. That is exactly the kind of story we want to tell. Entrepreneur journeys are not linear journeys. There’s a lot of navigation that goes on. This is really a entrepreneur’s story and that’s exactly what we want to tell. >>>

Bootstrapping With a Paycheck to Techstars: Nevin Shetty, CEO of Blueprint Registry (Part 5)

Sramana Mitra: Facebook is unique in its targeting capabilities. Talk about how you took advantage of that. What was the segment you were going after? What segment was converting for you? What did you learn about these nuances of positioning?

Nevin Shetty: As a wedding registry, we targeted people who were engaged.

Sramana Mitra: The status says they’re engaged, and you were marketing to that status.

Nevin Shetty: Correct. Lizzie and I would go to General Assembly classes and other online classes for marketing. Even though they’re engaged, people who live in New York are different from people in Texas. People who like Vogue are different from people who like InStyle magazine. We would then break out >>>

Successful Pivot from B-to-C to B-to-B: Inkling CEO Matt MacInnis (Part 4)

Sramana Mitra: What about the business model? Your hypothesis at that point was that you were going to digitize these textbooks, you were going to do the customer acquisition on the B2C side, and you were going to take a commission off that sale. What was the business model assumption with the publishers?

Matt MacInnis: They were taking all the rest of the money. It was a royalty-based model where Inkling was keeping a percentage of the sale of these titles. The publishers had all the leverage. The publishers got to set the price. They unilaterally controlled the transaction value and we just got a percentage of that. In hindsight, they were totally off. >>>