How to Keep Your Sense of Humor While Raising VC Funds

Jack Kuveke is the only guy I know who is brave enough to say what we’re all thinking about Warren Buffett.

“He’s the worst investor of all time. The guy doesn’t even drive a cool car and he’s lived in the same house for fifty years — truly a poverty mindset. Berkshire Hathaway is going to zero.”

If you sensed a subtle wink at the end of that take-down, you’re right on the money.

That line is part of his satire project Jabroni Capital, where Jack regularly roasts, flambés and skewers VC’s biggest names and trends with an impressive level of specificity. He can do that because while Jack may be a comedian, his bona fides are no joke. 

“I always wanted to be a comedy writer,” explains Jack, “and then tech worked out.”

Jack’s entrepreneurial prowess manifested early when he started building Minecraft servers with his twin brother. He eventually followed his interests into gaming cryptocurrency with an initial coin offering (ICO) called GAME Credits. 

By the end of his sophomore year GAME Credits had raised the largest ICO of all time, prompting him to drop out of college. Eventually, the enterprise blew up, leaving Jack an “unemployed…twenty-one-year-old idiot without a college degree,” Jack gamely recalls.

“There's a different scenario where I actually have a VC fund that's one hundred percent my money, and I own an island.”

Since sipping daiquiris on a private beach was out of the question, Jack kept grinding, eventually founding Hoodle, a tool for producing and disseminating small-group video calls for brands and influencers. Hoodle was Jack’s first foray into raising VC, and his experience there supplied him with plenty of comedic inspiration. 

Now Jack splits his time between Jabroni Capital, whose tagline is ‘as unreliable as your lead investor,’ and his fundraising consulting business, Raiseyourseed.com.

On a particularly funny episode of the How I Raised It podcast, Jack talks about his unorthodox journey to VC and satire writing. He shares insight on effective ways to engage investors, strategies for perfecting your email outreach and the importance of generating a sense of urgency around your product. 

Seven Tips To Raise It Like Jack

1. Keep it simple 

When Jack set out to fundraise for Hoodle, one thing quickly became apparent: the first-draft of Hoodle's pitch was too complicated and nuanced. 

So Jack organized a “Pitchapalooza” with friends, family, founders and, frankly, anybody who would listen. Jack and his team pitched twenty people in the span of forty-eight hours. Their goal was to aggressively refine Hoodle's story and come up with a new, easily repeatable deck that used the simplest terms possible. 

Jack ended up with a concise pitch deck of one hundred words; an investor could read it in under sixty seconds. 

It turns out that simple sells. This streamlined pitch deck propelled Jack to raise Hoodle’s $2.3M seed round a few months later.

2. Hook ‘em with traction or a gimmick

Jack hates long subject lines. He hates them so much that he has codified one simple rule when sending an email: subject lines must be four words or fewer. 

Jack eschews detail in favor of brutally effective brevity. He encourages startups to entice potential investors by immediately demonstrating traction or using “a gimmick to get them to open and then having a really killer first sentence hook.”

Here’s an example: when Jack was cold emailing for Hoodle, he would title his emails “seed round to checkout” in all lowercase, because then it looked like the email was forwarded from a friend or colleague. 

3. Lead with experience 

Jack used the same opening line for every message he sent: “I am a serial community builder: Minecraft servers 1 million+, crypto communities and, most recently, a startup accelerator.” Then he would link to relevant Twitter handles for his various projects. 

“I wanted investors to think, this guy is an insider, so I established credibility in my first sentence,” Jack explains.

4. Perfect your email strategy

Emails don’t have to be long and detailed in order to be effective. 

Here’s a five-part method for putting together a compelling email:

1. Include one clear sentence that says what your venture does in plain English — no buzzwords! 
2. Demonstrate traction by highlighting any big brand affiliations or investors. 
3. Name-check the companies against whom you’re competing, emphasizing your startup’s unique insight or philosophy. 
4. Wrap everything up by talking about your strong team as well as massive market potential. 
5. Put the ball in the investor’s court by saying something like, “We're raising our first round, would love to share insights on video and social commerce, what's the best way to discuss?”

Jack’s message was largely the same regardless of whether it was formatted for Twitter or email, with one exception: if Jack was communicating via email he would include a pitch deck, but if he was reaching out via Twitter he’d skip it.

5. Generate urgency 

If there’s one thing that Jack wants you to take away from this episode of How I Raised It, it’s that it’s your job to get momentum going for your deal. 

Jack learned this the hard way fundraising for Hoodle. After a number of pitches without big payoffs, Jack and his team realized that investors weren’t feeling any urgency to jump on board. 

So, Jack decided to put together a product launch, and, because it was a video product, invited VCs, angels and people in tech Twitter to a virtual launch event. 

“We also sent them a cheeky DM which said hey, can you come tell us if our product sucks? Then we DMed one thousand people on tech Twitter,” Jack says.

Ultimately, this strategy successfully drummed up new interest in Hoodle, and led to a fruitful meeting with a founder who encouraged Jack to…

6. Fake it till you make it 

In preparation for Hoodle’s launch, Jack met with a founder who pitched him a startlingly simple yet effective idea. “What if you email everyone you have ever spoken to who's not a16z and Sequoia and tell them you’re in second partner meetings with a16z and Sequoia?” Jack recalls. 

Sounds terrifying, right? 

Here’s the thing: it was technically true. Jack did have subsequent meetings lined up with those heavy hitters, but he was pretty sure they weren’t going to end up writing him checks. But Jack remembers his contact encouraging him to be bold anyway. 

“And so that night,” Jack recounts, “we got off the call at midnight and sent fifty or sixty emails in the middle of the night with no subject line…no punctuation, that said hey, we're in second and third party minutes with a16z and Sequoia. I've got a launch on Monday, should we catch up? We woke up to forty yeses overnight.” 

The tide was finally turning for Hoodle, and it all started because Jack and his team generated a modicum of momentum advertising their virtual product launch. 

7. Lean in to leveraging 

When it comes to fundraising, startups have a limited window of opportunity. That’s why Jack encourages founders to lay the table for success by scheduling meetings with investors within a short period of time. 

Then, if you get term sheets in the first couple of weeks of fundraising, you can use them as leverage in subsequent meetings. Jack’s strategy generates interest and urgency.

Jack stuck to this strategy fundraising for Hoodle, and it allowed him to bring on a couple of additional big-name angels and improve the terms on a number of deals.