Perhaps the most exciting moment in a new angel investor’s journey is that first check. The startup is doing amazing work, the sky seems to be the limit, and the math and story check out at least as far as you can tell. You double and triple check your thinking and then: click. The wire goes through. You’re officially an angel!

That moment is thrilling. But what comes after can be disorienting.

I found the early-stage investing world incredibly noisy. Everyone had an opinion: diversify, specialize, invest with a group, pick a sector, follow your passion, follow the math. I heard “just do ten deals,” but nothing concrete about how to pick that first one.

Then I talked to dozens of investors who make up the wonderful community at the ACA, and one thing became very clear: it’s not what you invest in, but how, that defines what you’ll get out of it. But it’s hard to find the right path for you: that place where who you are, what you value, and how you invest all converge into an authentic whole.

To shed light on that question, we decided to ask people who’ve already trodden that path. The answers came loud and clear in the recent ACA session I moderated, Finding Your Fit as an Angel Investor, featuring two seasoned investors: Juliet Lawrence and Matt Dunbar.

Their vantage points couldn’t be more different: Juliet is a finance professional who discovered angel investing through her work managing alternative investments. Matt is a veteran investor and co-founder of VentureSouth, one of the largest angel networks in the Southeast.

The result was a satisfying feast of fun and learning:

Start Small, Learn Fast

What struck me most about Juliet’s story was how she side-stepped the “go big or go home” trap that hurts many first-time angels. Coming from a corporate finance background, she didn’t jump in headfirst. Instead, she decided to start with small checks of $1,000 to $5,000 each and focused on learning, not winning.

“I wanted to learn before I leapt.”

Juliet viewed every deal, even the ones she only observed, as an experiment with tuition attached. Each taught her something new: how diligence really works, how group dynamics shape investment decisions, and how founders think when things go sideways.

As her confidence grew, so did her check size. More importantly, she became sharper about risk, process, and pattern recognition. Things like what makes for quality deal flow, and what signals trouble ahead.

She also stumbled into an insight: for most people, angel investing isn’t a solo sport. Joining the Houston Angel Network connected her with experienced peers who were generous with feedback and open about their mistakes. That community became both her classroom and her confidence booster.

“Not everyone can start with $25,000 checks,” Juliet said. “SPVs made it possible for me — and others — to learn by doing.”

I jotted down in my notebook:

• Angel investing is iterative — every check is data.
• Start small and focus on learning, not winning.
• Don’t chase returns early; chase pattern recognition.
• The right community multiplies your learning curve.

It’s Harder Than It Looks — But That’s the Point

These days, it feels like everyone on LinkedIn has “angel investor” in their bio. But what does that really mean? Does it just mean listening to a lot of inspiring pitches and writing checks?

When I asked Matt Dunbar what had surprised him most after years of investing, he didn’t say anything about writing checks or “doing deals”:

“It’s a lot harder than it looks,” he said. “The real work starts after you wire the money.”

From sourcing and diligence to deal structuring and post-investment support, angel investing is hands-on and humbling. Most startups fail, exits rarely arrive on schedule, and the path to return is long and uneven.

He had no illusions about the game: “We don’t control the market. But we can control our discipline.”

That discipline shows up most clearly in how VentureSouth manages exits. They treat it as an active, ongoing process and not something you hope for years down the line. The key, according to him, is to not miss the consolidation wave because market windows when acquisitions spike are fleeting, and catching them at the right time is critical.

I jotted down in my notebook:

• The check is just the beginning.
• Treat exits as strategy, not luck.
• Discipline beats intuition — process creates payoff.
• Patience is a skill, not a personality trait.

Think Portfolio, Not Pick

Another of Matt’s lessons was one I’d had obsessively beaten into my head from studying finance: it’s not which company to back, but how many that determines how well you’ll do. In other words, it’s all about the portfolio, not the individual stock.

“If you only make one or two bets, your odds of success are low,” he said.

Instead, he recommended treating your first few years like a lab. Spread $50,000 to $75,000 across ten to fifteen deals, even as low as $5,000 per company if needed. The goal isn’t instant returns. It’s to learn to recognize patterns coming from a large set of experiences. In other words, “get a lot of reps in before you go solo”.

The data supports him: diversification is the single most reliable hedge against the unpredictability of early-stage startups.

I jotted down in my notebook:

• One deal doesn’t make an angel.
• Ten to fifteen bets minimum for meaningful odds.
• Diversification isn’t optional. You must do it to survive.
• As you build your portfolio, you’re building judgment.

Who You Play With Matters

Both Juliet and Matt emphasized that finding your “fit” isn’t just about sector or stage, but also about belonging to the right community.

For Matt, that community is regional. VentureSouth started in Greenville, South Carolina, and now operates across the Southeast. Their focus is on helping local founders scale without leaving home.

If you want to be a part of helping companies grow in your own backyard, and not just obsess about backing unicorns, a regional investment strategy may be your ticket.

For Juliet, it was about inclusion and education, and joining groups that make it easier for newer investors to participate. She’s a big advocate for smaller check sizes and SPV structures so more people can get involved. This is particularly true if you come from a place where angel investing isn’t a common thing.

“The right group doesn’t just take your money,” she said. “It helps you grow as an investor.”

I jotted down in my notebook:

• Fit is relational, not just financial.
• The right group makes you smarter and braver.
• Shared learning beats solo guessing.

Play The Long Game

Matt and Juliet were both unanimous in agreeing that angel investing is a marathon, not a sprint. Returns take years. Mistakes will happen. But if you approach that journey with curiosity, discipline and a community mindset, you have a good chance of finding deep rewards far beyond the money.

“I started out chasing returns,” Juliet reflected. “Now I stay for the learning and the relationships.”

Matt echoed that sentiment through VentureSouth’s motto: Make money, have fun, do good.

Angel investing, as he reminded us, is about more than IRR. It’s about building ecosystems, supporting entrepreneurs, and creating value close to home.

I jotted down in my notebook:

• Angel investing rewards curiosity and endurance.
• Relationships compound faster than returns.
• Invest in people — founders, co-investors, yourself
• Success is building something bigger than your portfolio.

Final Thoughts For the Road

In the end, “fit” in angel investing isn’t just a financial decision. It’s a reflection of who you are, your appetite for risk, your curiosity, and the kind of impact you want to make.

If you find yourself staring at your first potential deal and wondering where to start, take it from those who’ve been there:

          Start small. Stay curious. Join a community.

Because in this world, how you invest matters as much as what you invest in.