When in Doubt, Consult

Consulting isn't glamorous. That's why it works.

One of my biggest slow bet wins came from a consulting deal. Half cash, half equity. The company sold for a very large number. That one deal probably made more than IdeaMensch generated in a decade.

I almost didn’t take it. I almost insisted on all cash, like I’d trained myself to do by then. And if the company hadn’t sold, the equity would have been worth nothing. Like every other equity deal I’d ever taken.

I took the 50/50 because I believed in the entrepreneur. That matters. But it was the exception, not the plan.

I love talking about IdeaMensch. It’s been one of the most meaningful projects of my life. But if I’m being honest, some of my best financial wins didn’t come from my own ideas. They came from helping other people build theirs.

Consulting on the side. Next to a day job. Real work for real people in exchange for cash.

Here’s how I’ve always approached it.

Most of my consulting happened in my twenties and early thirties. No family yet. I was willing to work late nights and weekends because the only person I was shortchanging was (mostly) myself.

It’s also the perfect early career move. You’re not just generating cash flow. You’re learning how other people build things, solve problems, and make decisions. Every consulting engagement made me better at my day job. The skill compounding alone would have been worth it even if the money hadn’t followed.

I’ve always consulted alongside a day job. That forced discipline. It meant I never promised more than I could actually deliver.

Think an hour a day. Not a second full-time job in disguise.

I preferred flat monthly retainers. Mostly because I hate tracking hours and the mindset that comes with it. Some months, I undercharged. Other months I overcharged. The goal wasn’t optimization or profit maximization. The goal was sustainability.

If consulting starts to feel heavy, you’ve already gone too far.

That line is the whole section. Read it again.

I set conservative expectations about what my work could accomplish, then worked like hell to beat them. I never marketed myself. Never announced availability. Clients came through word of mouth.

People don’t refer consultants who promise the moon. They refer the ones who quietly make things better, and deliver.

Over the years, I went through long stretches when I didn’t take on a single new client. I haven’t taken on a new one in almost ten years. When your calendar is full, say so. Scarcity isn’t a tactic. It’s a boundary. Consulting is meant to support your Slow Bets - not become the thing that consumes all your time and energy.

If you want scale, build a product. Consulting should stay small, controlled, and slightly boring.

I’ve always been upfront with my employer about my consulting work. That’s non-negotiable. Never work on side projects during work hours. Never use company equipment. If you can’t do it cleanly, don’t do it.

Actually, I’ve always encouraged my own employees to take outside opportunities if they have them. Heck, I’ve referred a ton of business to people. But the expectation has always been that any outside hustle can’t impact your day job.

And if you’re in a role where your compensation is so good that side work doesn’t make sense? Your job is your Slow Bet. Take the surplus and invest it directly into assets that compound.

Early on, I wasn’t really consulting. I was just helping people. Someone had a problem, I knew how to fix it, so I’d show up. No contract. No fee. No plan.

Over time, that turned into ongoing equity deals. Nobody wanted to pay cash to someone my age. I was unproven and happy to be in the room. So I took what I could get.

None of that equity ever turned into money. Not a single deal. But I learned more in those engagements than in any class or book. And every person I helped became someone who’d vouch for me later.

That’s when I switched to all cash. Cash buys freedom. Cash funds Slow Bets. Not someone else’s.

Eventually, I had enough of a track record to negotiate cash and equity. That’s where the real upside lives. The cash covers your time. The equity is a free option on someone else’s bet.

The 50/50 deal I opened with was one of those. It paid off in a massive way. But when in doubt, take the cash. The slow bets you build on your own are where you’re building true equity. Most of my consulting income went straight into ETFs. Boring, automatic, compounding in the background while I slept. But this is equity too.

Used correctly, consulting isn’t the destination.

It’s the engine.