From Bubble Gum to a Personal Bloomberg
How hacking your own tools is shaping the future of venture capital
When I was growing up, my dad loved the show MacGyver. For those who don’t remember, MacGyver was the kind of hero who could stop a bomb from exploding with nothing but duct tape, bubble gum, and whatever else happened to be lying around. The point wasn’t that he had the best gear. The point was that he could improvise, adapt, and win with whatever was in front of him.
That show stuck with me. A whole generation of us learned the same lesson: sometimes the bomb is ticking, the clock is running out, and all you have is the stuff in your pockets. What matters is whether you can make something work.
Right now, venture capital (and most other client service functions) feels like it’s in its own MacGyver era.
Everyone’s improvising
Most investors I talk to, from emerging GPs to established fund managers to family offices, are duct-taping together systems just to keep their relationships, insights, and deal flow from falling apart. We’ve all got a CRM (or three). We’ve all got some Slack (or Discord) groups, maybe a Notion doc or Airtable base, maybe a Zap or two firing in the background. And now AI (from note-taking to analysis) has entered the mix.
The result is messy. But it’s also a signal: we’re in a moment of improvisation that usually precedes a new category of infrastructure.
Finance had its version of this in the 1970s and 80s. Before Bloomberg standardized financial data, traders were scribbling notes, calling friends, and hacking together whatever feeds they could. The improvisers who survived that era didn’t just make money. They shaped what became the next operating system of the industry.
I think that’s where we are in venture right now.
Relationship arbitrage has never been more valuable
Venture has always been a business of relationship arbitrage. Who you know, who trusts you, and who you can connect has always mattered. But in today’s environment, it matters more than ever.
Markets shift in 30, 60, 90 days. Pricing changes at large enterprise tech companies that used to take a year now happen in a quarter. Founders and LPs are harder to reach, harder to win, and harder to keep close. The noise is relentless.
Which means this: being able to connect more worlds faster is the real advantage. Anyone can read TechCrunch. Anyone can scrape LinkedIn. But not everyone can remember the family office contact who loves applied AI in insurance, introduce them to the operator building a claims platform, and bring in the right co-lead GP who knows the backchannel.
That’s relationship arbitrage at scale. And it’s the only thing AI won’t replace. But maybe it can enhance personal context?
Why CRMs are only 60% solutions
Here’s the reality I’ve come to: off-the-shelf CRMs are only ever going to get you to 60% of what you need. They’ll store contacts, maybe log emails, and spit out some reminders. But relationships aren’t static. They’re living, dynamic, and deeply personal.
Every investor has their own workflows, quirks, and style. Some want tags, some want lists, some want nudges. No two people track relationships in exactly the same way. Which means no static CRM can ever give you the full picture.
But now, with AI, we’ve finally got the tools to build to 90%. Personalized, adaptive, evolving systems that actually work the way you think.
I’ve seen this firsthand. For roughly $200, in about nine days, I hacked together my own system I call Constellation, with Replit. My CRM plus Notion plus my Fathom AI notes plus GPT plus a few zaps. It’s duct tape and bubble gum, but it works (like a 6-year-old) to remind me of what I’ve learned and who I should connect with or what I should ask for. And the deeper I go, the more I see how much energy it gives me to keep moving through the uncertainty of building Stresswood.
Because here’s the truth: I always assumed I should use technology to patch my weaknesses. Missed follow-ups, scattered notes. But what if the real advantage is using technology to amplify your strengths?
That’s the revelation.
A long obsession, coming full circle
This isn’t a new fascination for me. My failed founder attempt fifteen years ago was a startup built around cultivating better networks. At the time, we had predictive analytics, some data scraping, maybe a LinkedIn export. It wasn’t enough. The tools weren’t there yet.
But I’ve never stopped being obsessed with this question: how do you actually connect and cultivate relationships at scale? How do you bridge the worlds that don’t talk to each other, and do it with intention?
That’s what pulled me into equity research at the start of my career. That’s what I’ve carried into venture. And now the technology finally exists to make it real.
Why this matters for the next cycle
The MacGyver era won’t last forever. The duct tape and bubble gum solutions will give way to more standardized platforms. But the improvisers who are experimenting now will be the ones who define the blueprint for what lasts.
In venture, that means:
LPs and GPs who build relationship intelligence into their DNA will have an edge that compounds.
Firms that treat relationships as infrastructure, not afterthoughts, will win the trust wars.
Emerging managers who embrace messy improvisation now will grow sharper instincts for the next operating system.
I believe we’re on the cusp of a new category: the Bloomberg Terminal of relationships. It won’t look like LinkedIn. It won’t look like Salesforce. It’ll look like a living system built for how humans actually connect and compound trust.
Closing
So yes, right now, it feels like the bomb is ticking and all we’ve got is duct tape, bubble gum, and a half-working Airtable base. But that’s exactly how new eras begin.
Because MacGyver wasn’t about the tools. It was about the ingenuity to use them in ways nobody else thought of.
And in venture, that ingenuity isn’t optional. It’s survival. And survival is producing industry-leading returns.