4Q4: Four Questions For … Taj Adhav, Leasecake

It wasn’t long after a stint in a Palo Alto, Calif., incubator with what was then a small, fresh Orlando startup Leasecake that Taj Adhav noticed something different this time around in business.

Adhav was about five years removed from one of Orlando’s most-successful tech exits ever, the $125 million acquisition by Google of Channel Intelligence, where Adhav was employee No. 8.

At the time, venture capitalists were firmly on the side of: “If we invest, you must move to Silicon Valley.” Ever since, however, that script has flipped.

“They said, ‘Go out to wherever you came from and build your company – investors will find you,'” he said.

They were right: Leasecake announced this week a $10 million extended Series A funding round led by Las Olas Venture Capital in Fort Lauderdale and PeakSpan Capital in New York.

“There’s now many capital sources in so many verticals and stages who believe in you, but they do need to find you,” Adhav said. “Please learn the market, because remember, they’re shopping for you too.”

We caught up with our old pal Adhav, whom we met when Leasecake was just a couple of days old, having just come out of a Startup Weekend in 2017.

Can you explain the feeling when you land this kind of investment?

It doesn’t just feel “good,” it feels empowering. I’m always inspired by those who believe in us. When you surround yourself with people smarter than yourself, who believe in what you started, it’s also humbling. Our team is made up of wonderful people of all skills and backgrounds. Some people remain outsiders along the way but support us and they, understandably, have their lives and sit on the sidelines and watch. There’s absolutely nothing wrong with that! But our team is simply fantastic. They chose to join us from the beginning, recognizing that one simple idea can transform businesses to reduce risks and protect their hard-won locations, building their dreams, their empire and legacy, not just in North America, but globally. It reaffirms our team’s belief in why they joined me. Let’s face it, they made a bet, much like I made a bet on a basic question, “If everyone in business leases or owns a location, where’s the app for that?” We’re all astounded that after several years of founding Leasecake, there are multi-billion dollar organizations still on spreadsheets. That is until they see Leasecake and say, “Where have you been all my life?”

What has building Leasecake been like in the last couple of years?

We operated out of a small bungalow in Winter Park for some time. Yes. It was humbling just as the pandemic hit, and despite all the nay-sayers – “Taj, the market is going to crash, get ready!” – we saw the opposite. We grew, and grew. Companies from all over signed up. All types of business operators came on board and paid for our services in advance. It was perfect timing, because our team also needed to see the market start buying despite what the world was going through. It continued to validate our business model – we had 4.5 FTE’s for quite some time! I look back and treasure those days, as we learned so much listening to the market.

What is your take on Orlando tech, as someone who has been involved a while?

The talent pool and capital is 100 times better than it ever has been in Central Florida. Early investors bet on jockeys, the horses, and then the entire race, if I can use the analogy. The world has changed, and I encourage creators, inventors and entrepreneurs to be fearless. There’s now many capital sources in so many verticals and stages who believe in you, but they do need to find you – please learn the market, because remember, they’re shopping for you too! It takes humility and sheer will. Not everyone is cut out for it, but believe in yourself – and remember that ideas are better when shared. Share your ideas freely – they’ll get stronger. Keep your mind open to the “Impossible Opportunities,” and then have the discipline to focus, win a key customer base with product-market fit, build a team who trusts in each other and execute. The scariest part is that it sounds so easy.

What are some important elements of seeking investment?

Three things: Humility, ferocious curiosity and willpower. Always. Stay humble, learn, and always ask for advice. Never ask for money. Iterate your idea, take feedback, stay humble, ask questions, learn, pitch, ask for advice, iterate, take feedback. See the pattern? And failure is always welcome – if you learn from it.

If you want to be the smartest person in any room, chances are you won’t get the backing. And please be very selective with whom you invite as a capital partner.

I recall telling a VERY large investor, “You’re not ready for us and not the right fit.” I’ll never divulge who it was, but their reaction was telling, cementing my decision. Remember from above, investors initially bet on jockeys – those they trust with their money. They believe in you – it’s humbling. It’s your job to earn their trust, and continue to build on it. If you choose your investors well, they’ll help you beyond just money, they’ll open doors to take you to the next level you never even saw. These things will happen when you realize that you choose who will invest in you, too! And only if you ask for their advice.