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?

Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 2)

Sramana Mitra: Okay. Let’s go back to this point where you have three high schools that you’re working with to validate your business model. How much were they willing to pay you?

Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 1)

This story is a great example of an EdTech company that has built a validated, bootstrapped, profitable business that can potentially be scaled using AI.

Building a Venture Scale Cyber Security Startup in the Age of AI: Alon Jackson, CEO of Astrix Security (Part 6)

Sramana Mitra: For both of these functions—the product definition side and the iterative product definition side, as well as the actual scenario mapping on the engineering side, are you using off-the-shelf tools, or using stuff that have you built yourselves? What does the infrastructure look like?