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 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

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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 7)

Sramana Mitra: All right. So then, last question. At this point, you have raised $40 million for this company, or has there been more money into the company?

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?

Building a Venture Scale Cyber Security Startup in the Age of AI: Alon Jackson, CEO of Astrix Security (Part 5)

Sramana Mitra: So, two questions on AI. First one is, as you said, there is a tailwind, clearly, because agentic AI this year in 2025 has started to take off, and we are doing this interview in June 2025. We have started hearing about agents quite aggressively all through this year. So, the vulnerabilities caused

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