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Playing Ping Pong in the Hurricane: Fundraising During Chaos

Apr 26, 2025

When the Winds Begin to Howl

It was September of 2008 and we had been actively funding Urban Planet Mobile since February of that year. Our first investor had committed to fund our new company with $500k paid out over the next 6-12 months with monthly wires coming in like clockwork. That month we received nothing. Nothing in October either. In fact, I couldn't reach that investor by email, phone, or fax until January the following year. He was in a hospital in Bangkok after the global meltdown occurred.

Imagine trying to play ping pong while Category 5 winds whip around you. That's what fundraising during the 2008 financial crisis felt like. Each time you positioned yourself for a return, the hurricane winds would shift unpredictably, sending the ball in an impossible direction.

Fortunately, I went to Macau in November with under 2k in all my accounts and a new investor completed the rest of that lost investment - about 250k. There's a reason they are called angels! It was like finding someone who brought their own weighted ping pong ball that could cut through the hurricane winds.

I went on to fund Urban Planet Mobile over the next few years to over $4 million, mostly through angels and strategic partnerships - the VC market was pretty closed. We learned to play our funding game despite the financial hurricane around us, adapting our strategy to the chaotic conditions rather than waiting for perfect weather.

Ping Pong Strategies for Hurricane Conditions

  1. Perfect Your Technique

Be perfect. Seriously, your presentation, deck, documentation, pitch and ask must be really tight. Normal early investors whose 80% of their portfolio is chugging along fine are now distracted daily watching it move up and down. You must be focused, crisp, and clear.

In hurricane-force fundraising, every stroke must be flawless. When winds are howling at 150 mph, a slight misstep means your ping pong ball disappears forever. Like professional players who practice the same shot thousands of times, refine your pitch until it can cut through chaos. Investors battling their own financial storms won't tolerate sloppy play.

  1. Make Your Shots Count

Highlight any and all traction both in your company and raise. Investors want to see that your project/product is getting traction and will generate the best non-dilutive capital - revenue. Also, highlight progress in your raise.

In normal conditions, you might get away with fancy play and unnecessary flourishes. In a hurricane, each shot must be purposeful and powerful. Your metrics of success – customer acquisition, revenue growth, user engagement – are like perfectly placed shots that even hurricane winds can't knock off course. When investors see these powerful returns, they're more likely to brave the storm to play with you.

  1. Play More Games

Expect smaller checks so increase your activity.

During calm weather, you might play one high-stakes ping pong match. In a hurricane, prepare to play dozens of smaller games simultaneously. Each potential investor may only commit to a fraction of what they would in stable conditions. Like a ping pong player who can no longer rely on a single tournament win, diversify your fundraising tournaments and be prepared to play many more matches to achieve the same result.

  1. Design Special Hurricane-Proof Equipment

Be creative in your offer and consider warrants so investors can participate more fully when the market calms down (70% of my investors invested more than once).

Standard ping pong equipment fails in hurricane conditions. You need specially designed paddles and nets that function in extreme weather. Similarly, traditional equity structures may be inadequate during financial chaos. Design investment terms that acknowledge current difficulties while providing outsized returns when conditions normalize – like a ping pong paddle weighted to cut through wind but still maintain control.

  1. Find Players from Different Leagues

Talk to everyone about your project - not the normal "angel" community only - thoracic surgeons don't see huge income drops due to tariffs.

Professional ping pong players might avoid hurricane matches altogether, but enthusiasts from other sports might be intrigued by the challenge. Look beyond traditional investment communities to professionals whose incomes remain stable during downturns. While tech investors were sheltering from the storm, medical specialists and other professionals with protected incomes were often still looking for interesting opportunities – they just needed to be invited to the game.

  1. Travel Light and Conserve Energy

Keep your burn rate as low as possible - it is a competitive advantage. The only reason we survived is because I stockpiled the initial wires.

Playing ping pong in a hurricane requires extraordinary energy conservation. Every movement must be efficient; every resource carefully managed. Minimize your operational expenses to extend your survival time. Like athletes who carefully manage their caloric intake during extreme competitions, your startup must operate with exceptional efficiency to last until conditions improve.

  1. Maintain Your Physical Condition

And finally, focus, truly focus on your own mental, physical, and emotional health. Take walks, watch the alcohol, talk to non-biz related friends, eat well, and sleep. This shall pass so don't screw up your emotional or physical health.

No athlete can perform in extreme conditions without outstanding physical conditioning. Fundraising during chaos similarly demands peak personal condition. Maintain exercise routines, healthy eating habits, and adequate rest. The entrepreneur who neglects self-care is like the ping pong player who shows up dehydrated and exhausted – unlikely to win regardless of skill level.

  1. Train with Master Coaches

Work with a coach, mentor, previous entrepreneur, etc. to help you "blue ocean" your marketing, strategy, or fundraising.

Elite athletes rely on specialized coaches, particularly when preparing for unusual conditions. Find mentors who have successfully navigated previous downturns. Their pattern recognition and strategic advice can help you identify non-obvious opportunities. Like the ping pong coach who teaches special hurricane techniques, experienced advisors can help you adapt your approach to chaotic conditions.

  1. Join a Hurricane-Ready Team

Consider setting up or adding to your Board of Advisors/Industry Advisors to grow networks.

No one plays hurricane ping pong alone. Build a team of advisors with complementary skills and networks. Each brings different expertise in navigating extreme conditions, from technical knowledge to investor relationships. Like assembling a special team for extreme weather competitions, your advisory board should include individuals specifically chosen for their ability to add value during tumultuous times.

Mastering the Hurricane Game

The entrepreneurs who succeed in fundraising during chaos aren't necessarily the most naturally talented – they're the ones who adapt most effectively to extraordinary conditions. They perfect their technique, make their shots count, play more games, design specialized equipment, find unconventional players, travel light, maintain peak condition, train with master coaches, and build hurricane-ready teams.

When the financial winds eventually calm, you'll find yourself with more than just capital – you'll have developed the resilience, efficiency, and adaptability that create lasting competitive advantages. The skills you develop playing ping pong in a hurricane will serve you well even when you return to normal conditions.

Remember: the hurricane always passes eventually. The question is whether you'll still be in the game when it does.