Demystifying Startup Fundraising: Gagan Singh Drops Gems on The CTO Show

Picture this: you're navigating the labyrinth of startup fundraising, unsure if you're on the right path, but then—bam!—Gagan Singh, CEO of WOWS Global, enters the scene like a seasoned guide, map in hand. On The CTO Show with Mehmet Gonullu, Gagan took us on a wild ride through the world of venture capital, leaving no stone unturned. Whether you’re a rookie founder or a battle-worn entrepreneur, this episode had something for everyone.

The Unvarnished Truth About Startup Fundraising

We’ve all heard the romanticized tales of fundraising: “I pitched, the VC smiled, and next thing I knew, I had millions in my account.” Well, Gagan is here to tell you that those stories are about as real as unicorns. Fundraising isn’t a quick trip to the bank; it’s more like a marathon through a jungle—with a few surprise plot twists.

Gagan, who’s been knee-deep in Southeast Asia’s venture capital trenches for years, shared some refreshingly honest insights into the rollercoaster ride of raising capital, especially in today’s frosty investment climate.

Cap Table Catastrophes: The Silent Killer

Cap tables. Yeah, we know—just hearing the phrase can make your eyes glaze over. But Gagan made it clear: ignore your cap table at your peril. He likened bad cap table management to "building a house on quicksand." And here’s the kicker: a lot of founders are out there winging it with Excel spreadsheets. Big mistake.

"Many founders are flying blind," Gagan warned. They give away too much equity too soon, and by the time they hit Series A, they’re left with a sliver of the pie. Gagan’s advice? "Stop the spreadsheet madness and get professional tools." Your cap table isn’t just a legal formality—it’s your startup’s lifeline.

Brace Yourself: The Funding Winter Is Here

If you’ve been feeling the chill of the “funding winter,” you’re not alone. Gagan painted a stark picture of Southeast Asia’s funding landscape, where total startup investment plunged by a jaw-dropping 65% in 2023. But it’s not all doom and gloom. Gagan likened it to a “much-needed market detox.”

The days of landing massive checks on the back of a glossy pitch deck are long gone. Investors want more—they want real businesses that deliver value, not just hype. And honestly? Gagan's all for it. He believes this shift is pushing startups to focus on sustainability, which can only be a good thing in the long run.

Secondary Transactions: Your Secret Weapon

Now, let’s talk about something founders don’t often discuss: secondary transactions. If you’ve been grinding away at your startup, holding onto shares like a dragon guarding treasure, but can’t find a way to cash in, this one’s for you.

Gagan knows the frustration all too well. As CFO of Deliveree, he sat on a mountain of shares but had no way to access liquidity. His solution? Secondary transactions—selling off a portion of your shares before the big IPO or liquidity event. It’s like finally being able to dip into that retirement fund without waiting decades.

And that’s where WOWS Global comes in. Gagan's mission? To make secondary transactions smoother and more accessible for founders so they can get the liquidity they need without waiting for the stars to align.

Relationships > Tech: The Unspoken Rule of Private Markets

While we love our tech tools at WOWS Global (who doesn’t?), Gagan reminded listeners of one crucial fact: "Private markets are still a people business." You can have the fanciest tech stack in the world—cap table management, virtual data rooms, ESOP platforms—but without strong relationships, you're going nowhere fast.

Building real, human connections with investors is still the secret sauce in securing funding. WOWS Global’s platform helps with the tech, but the relationships? That’s on you, founder.

Why This Episode Is a Must-Watch

Whether you're just dipping your toes into the world of fundraising or you’re already planning your exit strategy, this episode is pure gold. Gagan breaks down the realities of startup life with zero fluff, serving up advice on everything from cap tables to liquidity to weathering the funding winter.

So grab a coffee, put on your headphones, and buckle up for one of the most insightful startup conversations you’ll hear this year.

Ready to Take Your Startup to the Next Level?

If you’re tired of flying blind and ready to make your startup fundraising journey a whole lot smoother, why not talk to the experts? Book a call with Gagan and get the advice you need to start raising capital the right way.

Watch the full episode here