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🕑 Read Time: 4.5 Minutes
The VC Game Looks Wild From the Outside...
Unicorns. 10x returns. Founder dinners with oat milk Negronis.
But inside the machine?
It’s mostly waiting.
➡️ Waiting for founders to reply
➡️ Waiting for product-market fit
➡️ Waiting for your carry to mean something
VC life is a lot of hurry-up-and-wait—with a constant undercurrent of FOMO and panel invites.
So how do I stay sane? Or better yet—human?
I pick up side quests.
Credit to DJ Chris Palacio for all the music mixes and mashups over the years, whose insight reminded me that the best work we do often starts far outside any cap table.
🎮 What’s a Side Quest?
In gaming, side quests are optional missions. Not part of the main story, but usually the ones you remember most.
In VC, side quests are the personal pursuits that keep us from turning into spreadsheets with headshots.
For me, that’s:
🏃 Running Tough Mudders
🏀 Coaching my kids’ basketball and volleyball teams
🎓 Serving on the board at my alma mater, USF
None of it fits in a pitch deck—but it feeds something deeper.
Side quests aren’t distractions. They’re what keep me sharp while my day job chases SaaS rocket ships and AI tailwinds.
And I’m not alone.
Rudemil Valeros, Max Diez 2024
🎧 Meet the VCs with Actual Lives (and Rhythm)
Some of the best investors I know don’t just source deals—they make beats, mix tracks, or design merch in their downtime.
Some are aspiring DJs, spinning sets on weekends instead of sliding into founder DMs.
Others are former musicians, still writing songs, producing tracks, or recording in home studios.
My managing partner at 25v, EJ Pineda, channels his creative side by designing viral merch for K-pop events around the country. He didn’t just make swag—he built a micro-brand inside a fandom, from the ground up. It’s bold, obsessive, and awe-inspiring.
Creativity isn’t a detour—it’s part of the engine.
And when it connects back to the mission, it is even better. Just check out what we did for USF—custom merch, meaningful partnerships, and community-focused design. (I’ll drop a photo below—worth a look.)
🛠 Why Side Quests Matter
1. Range > Tunnel Vision
The best VCs don’t just read trend reports—they live lives. Cooking, designing, DJing, parenting, running—all of it builds empathy, intuition, and depth. That’s what founders respond to.
2. Keeps You Grounded (and Less Insufferable)
Side quests pop the VC bubble. Coaching youth teams reminds me of what leadership looks like. Getting smoked in the mud reminds me that grit isn’t theoretical.
3. Best Ideas Happen Outside the Boardroom
Breakthroughs don’t come from webinars. They come while sketching a merch line, planning a community event, or watching your kid’s team claw back from a 10-point hole.
4. Founders Want Partners, Not Tourists
If your only hobby is “mentoring,” you’re not fooling anyone. Founders want people who show up in the real world, not just the cap table.
More than 30 years ago, before I ever thought about finance, I thought I was destined for action movie glory.
Not Hollywood glory—more like low-budget, high-kick martial arts legend in my own head. That side quest led me to a short film project at the College of San Mateo. We shot it on Super 8mm, with duct tape and pure grit.
This clip is from that film.
It’s a little grainy. A little wild. But it was mine.
It reminds me that discipline lives in the doing, not the talking.
There’s no shortcut to grit.
🧾 The Narrow Game Is for NPCs
If you’re in VC with no side quests, congrats—you’re playing on easy mode. But that game won’t teach you much. And it won’t help you connect.
I didn’t take the straight path. I started in real estate. Built teams. Made mistakes. Learned by doing. My side quests aren’t distractions—they’re the foundation. They gave me the grit, perspective, and instincts I needed to back people who remind me of the journey.
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📈 TL;DR
If your only side quest is “crushing it,” you’re missing the real compounding.
Start something on the side. Coach. Build. Create. Volunteer. Spin vinyl. Design merch. Do something that doesn’t require a pitch deck or a pitch.
It might be the best investment you ever make—even if your LPs never hear about it.
Maximillian Diez
GP, Twenty Five Ventures
P.S. Stay with me on this journey.
