High Stakes Guessing

Hey there,

Welcome to where I write about my journey from a stable Big Tech Software Engineering job to the wild and volatile world of Venture Capital.

You know what's funny? When I was a SWE, I used to think VCs just threw money at cool ideas and collected their billions. Now I'm on the other side, and let me tell you-this is some high-stakes poker where most hands are garbage, but you've gotta play enough to hit that royal flush.

For those who haven't been indoctrinated into VC-speak yet, seed stage is basically the awkward teenage phase of startups. They're past the "my mom thinks this is a good idea" stage (friends and family/pre-seed) but not quite at the "we have actual customers and revenue" phase (Series A).

It's where a founder with a prototype or maybe some early users gets their first real money to build something that might actually work. Or, you know, spectacularly flame out. Either way, it's where the magic/tragedy happens.

And for investors like my firm? It's where we place our bets on people who might be the next Airbnb founders (who, by the way, got rejected by like everyone before getting their first real check). The stakes are insanely high-most will fail, a few will return our money, and if we're lucky, one or two might actually make us look like geniuses.

Long Angle is a private, vetted community connecting high-net-worth entrepreneurs and executives with institutional-grade alternative investments. No membership fees.

Access top-tier opportunities across private equity, credit, search funds, litigation finance, energy, hedge funds, and secondaries. Leverage collective expertise and scale for better terms.

Invest alongside pensions, endowments, and family offices. With $100M+ invested annually, secure preferential terms unavailable to individual investors.

Apply to Join

Let me break down why I wake up in some nights wondering if I've made terrible decisions:

Information Asymmetry Is a B*tch: You know who knows everything about the startup? The founder. You know who knows almost nothing? Me, the investor trying to decide if I should give them millions of dollars. Cool system, right? We're basically making massive decisions with like 20% of the information we actually need.

Traction? What Traction?: Most seed startups have zero revenue, zero customers, and zero proof their idea will work. So what exactly am I analyzing here? A PowerPoint and a dream, basically. My spreadsheet skills from BigTechCo are essentially useless when there are no numbers to crunch.

Team Risk Is Everything: Since there's no business to evaluate yet, we're really just betting on people. Can this random 19-year-old Stanford dropout actually build and run a company? Who knows! But I've got to make a yes/no decision anyway. It's like speed dating but with millions of dollars on the line.

The Follow-On Nightmare: Here's a fun stat that keeps me up at night: only about 13% of seed-funded companies make it to Series A. That means roughly 87% of my portfolio is probably going to struggle to raise more money. Cool cool cool, no pressure.

I sometimes wonder if I should have just kept writing code in my comfortable BigTechCo job where success was measured in completed sprints, not in whether I could spot the next unicorn before anyone else. But where's the fun in that, right? 🙃

After watching the partners at my firm and talking to other seed investors, I'm starting to see patterns in how the best players in this game operate:

They're Obsessed With Founder-Market Fit: The top investors I've seen don't just ask "is this a good idea?" They dig deep on "why is THIS founder the right person to solve THIS problem?" Did they experience the pain point personally? Do they have unique insight or experience? One partner told me, "I'm looking for the founder who couldn't NOT start this company"-which sounds cheesy but is actually spot on.

They're Religious About Ownership: The math of venture is brutal-you need massive winners to make the model work. The best seed VCs target 10-15% ownership in each company because they know if they get lucky and hit a unicorn, that stake needs to return their entire fund. I watched a partner walk away from a "hot deal" because the ownership wasn't there, and I thought he was crazy... until he explained the math.

They Take Enough Shots on Goal: This isn't like public market investing where you can be right 60% of the time and crush it. In seed, you might be wrong 90% of the time and still succeed if your winners are big enough. The top firms know this and build portfolios of 30-50 companies per fund. It's a numbers game, but with very specific numbers.

They Actually Help Their Companies: The best seed VCs aren't just check-writers-they're company builders. I've seen partners spend entire weekends helping portfolio companies redesign their product, make customer intros, or interview key hires. The difference between passive and active investors at seed stage is night and day.

They Navigate the Signaling Minefield: There's this whole meta-game around signaling in VC. If a big-name firm invests in your seed but doesn't follow on for Series A, it's like getting a scarlet letter. The best seed VCs are super transparent about their follow-on strategy and actively help companies find their next investors.

With approximately eight billion seed funds now competing for deals (slight exaggeration, but it feels that way), how do the top firms differentiate themselves? A few patterns I've noticed:

They Build Proprietary Deal Flow: The best firms never rely on inbound-they build networks that surface deals before anyone else sees them. Some run scout programs (paying well-connected people to find deals for them), others build content that attracts founders, and some just hustle harder. One partner I know takes 30 founder coffee meetings a week. Thirty! I'm exhausted just thinking about it.

They Go Deep On Specific Themes: The days of the generalist seed investor are numbered. The top firms now specialize-becoming the go-to investors for specific sectors like fintech, climate tech, or AI. When a founder is building in that space, they want the investor who lives and breathes their industry, not a generalist who dabbles.

They Create Actual Value Beyond Money: Platform services are the new battleground. Some firms have in-house recruiters, PR teams, and even engineers to help portfolio companies. Others host founder summits, create peer groups, or offer specialized training. The bar keeps rising on what "value-add" means.

They Move Fast With Conviction: In a world where hot deals close in days not weeks, speed is a competitive advantage. The best seed VCs have streamlined their process to make decisions quickly and with conviction. I've seen partners make multi-million dollar commitments after just two meetings with a founder. It's terrifying and impressive.

Long Angle is a private, vetted community for high-net-worth entrepreneurs, executives, and professionals across multiple industries. No membership fees.

Connect with primarily self-made, 30-55-year-olds ($5M-$100M net worth) in confidential discussions, peer advisory groups, and live meetups.

Access curated alternative investments like private equity and private credit. With $100M+ invested annually, leverage collective expertise and scale to capture unique opportunities.

Apply to Join

What's fascinating about seed investing is how it blends quantitative and qualitative decision-making. There's a science to it-portfolio construction, ownership targets, market sizing-but there's also an art.

The best investors develop this sixth sense about founders. They can tell within minutes if someone has that special combination of vision, adaptability, and grit. It's pattern recognition built from seeing hundreds of founders succeed and fail.

I'm still developing that pattern recognition, and honestly, I question my judgment constantly. Did I just pass on the next Stripe because the founder seemed a little awkward? Did I just champion investing in a complete dud because the founder went to my alma mater and I had unconscious bias? The self-doubt is real.

But that's the game. Seed investing is making high-stakes decisions with incomplete information, guided by both data and intuition. It's embracing uncertainty while still having the conviction to write the check.

Six months into this new career, do I regret leaving my cushy engineering job for the chaos of seed investing? Some days, absolutely. The stress is different-instead of worrying about a bug in production, I'm worrying about whether I just invested millions in a company that will implode next month.

But there's something addictive about this work. Every day I meet founders who are pouring their souls into solving meaningful problems. I get to be a small part of their journey, helping them navigate from idea to reality. When it works, it's magical.

And let's be honest-the potential upside is pretty compelling too. If I can help find and fund the next breakout company, the economics are... significant. Though right now that feels about as likely as winning the lottery while being struck by lightning.

So for now, I'm embracing the chaos, trying to absorb everything I can from the partners who've been doing this for decades, and hoping that somewhere in our portfolio is that one company that will make everyone forget about all our inevitable failures.

Would love to hear from others who've made similar career jumps. Did you leave a stable tech job for something completely different? How's it going? Drop me a comment below!

Until next time!

Signing off and signing zero checks,

SWEdonym