You're a founder who just sold your first product. Revenue is growing. The team is clicking. Some cash is piling up in the bank.

Now founders are sliding into your DMs asking if you'll invest in their companies. You think, "Why not? I'm killing it. I know this space inside and out. This should be easy."

But angel investing while running a startup is like getting a second full-time job that pays you in 7-10 years. Maybe. If you're lucky.

And most of your investments will crash and burn.

Still reading? Good. Because when done right, this can be one of the smartest moves you'll ever make.

Does being a founder help you invest?

Absolutely.

When you've lived through the absolute chaos of building a company, you understand what founders are actually dealing with.

You know that beautiful pitch deck means absolutely nothing when your best engineer quits three weeks before launch. You've been there. You survived it.

This founder empathy matters more than you think.

When a founder tells you they pivoted twice in six months, you don't automatically write them off as flaky. You understand that sometimes the market screams at you, and you have to move fast.

But here's what's even more valuable: you develop evaluation frameworks that professional investors miss completely.

Some founder-investors look for grit and determination above everything else. They only evaluate founders whose ideas already excite them. Then they assess: can this person push through walls?

Others focus on the idea first. They've watched too many gritty, determined founders waste years on terrible ideas. Even the hardest workers can't force a bad idea to succeed. The market doesn't care how hard you hustle.

Neither approach is "right." They're just different frameworks that come from actual operator experience.

How do you make time for this?

Let me be brutally honest: you probably don't have time. Not at first, anyway.

Successful angel investors set aside a few hours per month for advisory roles with their portfolio companies. That's just the helping part. It doesn't include sourcing deals, doing diligence, or making investment decisions.

Your startup is already consuming 60-80 hours per week. Where exactly are you going to find the extra hours?

The answer: you have to be ruthless about priorities. Here's what actually works:

Build a systematic deal flow engine. You can't invest in companies you never see. Three strategies that work:

• Attend accelerator demo days and startup events consistently
• Join top accelerators as a mentor (you see companies during the entire program before deciding)
• Build an X following where you share genuinely useful insights, not humblebrag nonsense

The key word is "systematic." You need a repeatable way to see deal flow, not random coffee chats.

Block the time or it won't happen. Put 2-3 hours on your calendar every single week for angel investing. Use that time to talk to companies, research markets, stay current. Protect it like your life depends on it. Because your startup will always feel more urgent.

_What do you need to start?

Three things: money, a strategy, and commitment.

Money. Never write just one or two checks. You need a portfolio.

If you're just starting out, your first investments will probably go to zero. This isn't pessimism. This is reality. You're learning an entirely new skill.

Try $1,000 per company at first.

Don't invest money you need for your business or your life. This is patient capital that might take 10+ years to return anything. Maybe never.

Even if you don't have money yet, start practicing. Look at every company at demo days. Pick which ones you find most interesting and why. Write it down. Track them for a few years. See if you were right.

Some successful angels did this for 5-7 years before writing their first check. They learned which patterns actually predict success without losing a dollar. Smart.

Strategy. You need an actual investment philosophy, not just "invest in cool stuff."

What types of companies will you invest in? What stage? What geography? What sectors?

But more importantly: What is your unfair advantage as an investor?

Maybe you have deep domain expertise in a specific vertical. Maybe you're exceptional at recruiting. Maybe you have a massive network of potential customers.

One angel leveraged their Y Combinator network. Most first-year investments were YC companies. Their pitch: "I'm a YC alum who's been through this." That was enough.

Another angel had no network when they started. So they went to four startup events per week. FOUR. For years. Now they don't need to go to events. But they put in the work first.

Figure out what you bring beyond money. Because if you're just writing checks, you're not valuable. There's always someone with more money than you.

Commitment. You cannot do this halfway.

If you invest in a company and it starts winning, you need reserve capital for the next round. Running out of money for follow-on investments is how you get diluted into nothing. You find the winner, then you can't participate in the upside. Brutal.

Set a concrete minimum. "I'm going to invest in at least 30 companies over the next four years." Write it down. Tell people about it. That commitment forces you to stay active even when your startup is imploding.

Prepare to suffer through the first 20 investments. This is where most people quit. The beginning is absolutely brutal. You don't have a track record. You don't know how to articulate your value. Founders don't think of you when they're raising.

But after 20-30 companies? Everything shifts.

You can finally say things like: "I invested in three healthcare companies doing similar things. They all tried approach A first, and it didn't work. Then they pivoted to approach B. I know your space and could help you skip that expensive mistake."

That's compelling. That's differentiated. That gets you into deals.

The referrals start flowing. Your portfolio companies introduce you to other founders. The benefits compound exponentially.

But you absolutely must survive those first 20 deals.

Should you do this or are you just suffering from FOMO?

If you're a first-time founder who just raised your seed round six months ago, this is absolutely not the right time. You need every single ounce of energy focused on your company. Your investors gave you money to build something, not to cosplay as an investor.

But if you're a second-time founder who deeply understands your market, has some actual liquidity, and genuinely wants to help the next generation? Angel investing can be one of the most rewarding things you'll ever do.

The key is radical honesty about whether you have the time, the capital, and the commitment to do this properly.

Just don't treat this like a hobby. It's not. It's a second job that requires real work, real capital, and real long-term commitment.

Start small. Build systems that scale. Push through the brutal early phase when nobody knows who you are. Write enough checks to build an actual statistical portfolio.

And please, for the love of all things magical, don't write two checks and think you're done. That's not angel investing. That's just gambling with a fancy name.

‍