Building a Venture Scale FinTech SaaS Startup: Mike Whitmire, co-founder and CEO of FloQast (Part 4)

Sramana Mitra: How does the competitive landscape map out?

Building a Venture Scale FinTech SaaS Startup: Mike Whitmire, co-founder and CEO of FloQast (Part 3)

Sramana Mitra: And how long did that $6.5 million last?

Mike Whitmire: We did extremely well in 2016 and the first half of 2017. We more than tripled our recurring revenue. Then we were approached proactively about raising another round. The investor was great, the terms were strong, and I was ready to scale further. We fielded a few term sheets, found the right partner, and raised our Series B—$25 million led by Insight.

Building a Venture Scale FinTech SaaS Startup: Mike Whitmire, co-founder and CEO of FloQast (Part 2)

Sramana Mitra: So, when you started going after companies that looked like Cornerstone, were you doing that as a bootstrap company or a venture-funded company?

Mike Whitmire: We had taken a small seed round of funding. We raised $1.3 million at the time to build out the first iteration of the product and prove we could go to market. We were working with a small budget because I wasn’t in a position to burn a lot of cash. I had to be very prudent with the funds we had.

Building a Venture Scale FinTech SaaS Startup: Mike Whitmire, co-founder and CEO of FloQast (Part 1)

Mike has raised over $300M and built an over $250M ARR FinTech SaaS business. Now, AI offers FloQast an opportunity to further strengthen their product roadmap with deep domain knowledge.

Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 6)

Sramana Mitra: What else is interesting in the strategy or in any moves that you’ve made leading up to now, in 2025? What else is worth discussing in your journey?

Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 5)

Sramana Mitra: So, you were acquiring families through SEO mainly.

Daniel Santos: Yes, primarily SEO.

Sramana Mitra: So, that was not limited to South Florida anymore?

Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 4)

Sramana Mitra: So, you were acquiring families through SEO mainly.

Daniel Santos: Yes, primarily SEO.

Sramana Mitra: So, that was not limited to South Florida anymore?

Daniel Santos: Not at all. At that point, we started working with families internationally and across many U.S. states.

Sramana Mitra: Around 2018, how many families are we talking about?

Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 3)

Sramana Mitra: Online’s fine. I’m not necessarily thinking that you’re already on AI in 2016–17, because that’s definitely not the time when AI was as pervasive as it is today. So, let’s go back to 2016–17. Tell me more about how the business was progressing. How many schools were you catering to in 2016–17? How were you finding them? How were you doing the sales process?