24 Years of Side Hustle Advice

What does 24 years of hard-won entrepreneurial lessons look like in one place?

Here are the biggest ideas from over a decade of building side hustles, interviewing hundreds of entrepreneurs, and learning what actually works.

This is a collection of honest, practical principles — some learned through success, some through failure — that can help you start smarter, grow faster, and keep going when things get hard.

Tune in to Episode 732 of the Side Hustle Show to learn:

how to find your real motivation and why it matters more than the idea itself
the mindset shifts that separate side hustlers who succeed from those who stall
practical frameworks for getting started, marketing your business, and knowing when to quit

Table of Contents show

1. Find Your Why

A lot of people start with, “I want to make extra money.” But you need to go deeper: ask why, then ask again, like an annoyingly curious five-year-old.

Maybe you want more breathing room in your budget. Why?
You want to pay off debt or take a family trip. Why?

Keep drilling down and eventually you land on something like: “I really value having autonomy over my time.”

That is the real driver, and it’s what will keep you going when things get hard.

2. Inspiration Is Temporary — Act Fast Before It Dies

When a side hustle idea strikes, inspiration has an expiration date.

Do everything you can to build positive momentum before it fades — register a domain, put up a product for sale, make your first offer. Do the easy part first.

Momentum breeds results, and results breed more momentum. If you can take action before inspiration expires, you’ll be much better off.

3. Ideas Are Like Buses — There’s Always Another One Coming

Miss the window on one idea? Don’t stress.

As Richard Branson put it, “Business ideas are like buses. There’s always another one coming.”

Missing one opportunity is not the end of the road.

4. Be Obsessed

It’s hard to compete with someone who’s truly obsessed with a topic. Credit card points and miles are a good example — plenty of people enjoy the game, but they’ll never out-compete the people who live and breathe it every single day.

When evaluating ideas, ask yourself: what do you never get tired of talking about? What still lights you up years later?

That obsession is a real competitive edge.

5. Follow Curiosity, Not Passion — One Experiment at a Time

If you don’t have a single burning obsession, follow your curiosity instead. Run one experiment after another. Test stuff.

Give yourself permission to try things without the pressure of them needing to be permanent.

One recent experiment I made was publishing an AI-generated episode. The audience didn’t love it, but it was worth testing.

My Facebook content monetization effort was also shut down after the results didn’t justify the time.

Both were honest experiments. Neither was a failure in the way most people think.

6. Money Comes from Solving Problems

A business is just a repeatable system for solving a problem. A lot of lists about “ways to make money” dance around this truth, but it’s the real foundation.

People are online for one of two reasons:

to solve a problem
or to be entertained

If you can solve a specific problem for a specific customer, it’s much easier to find an audience and start making money than if you’re trying to out-entertain Mr. Beast or ESPN.

7. Pain Pills vs. Vitamins

If you have a splitting headache, you go straight for the Excedrin. If you forget your vitamin today, it’s probably fine.

Pain pills are much easier to sell than vitamins.

What’s the urgent, expensive problem you can take away from your customers? The more your offer feels like a pain pill — something people desperately need right now — the less convincing you’ll have to do.

8. If You Can’t Be First, Be Different — If You Can’t Be Different, Be Better

Worried someone already built your idea? Jonathan Mendonsa from ChooseFI shared this line on the show: “If you can’t be first, be different.”

When he entered the financial independence space, there were already dozens of blogs — but very few podcasts. So that’s where ChooseFI focused and found its audience.

And if you can’t be different, be better. Look for the gaps, the small tweaks, the iterations that improve on what’s already out there. Leapfrog the competition.

9. Antelopes, Not Mice

There’s a proverb about a lion on the African savannah. It could chase antelopes or chase mice. Either way takes effort, but only one feeds it for a week.

When evaluating a business idea, ask: even if this works, is the reward big enough to justify the effort?

Make sure you’re aiming at the antelope.

10. Ask “What If This Works?”

We spend a lot of time thinking about how to avoid failure and minimize risk. Both matter. But you also have to ask: what if it actually works?

Look at someone 3 to 5 years ahead of you on the same path.

What does their day-to-day look like?
Is the income where you’d want it?
Do they have the freedom you’re after?

Aim for asymmetric bets — minimize your downside, but swing for a big enough upside that one win erases all the misses.

11. Stop Saying “I Don’t Have Time”

One phrase I have tried to remove from my vocabulary is “I don’t have time.” And I replaced it with the more honest version: “I prioritized something else.”

We’re all dealt the same number of hours in a week.

If you want to move forward on your own agenda, protect the bookends of your day.

Even 15 to 30 minutes first thing in the morning and last thing before bed, spent proactively on your work before reacting to everyone else’s, can add up fast.

12. Bullets Before Cannonballs

This principle comes from Good to Great by Jim Collins. Before going all in with a cannonball, fire some bullets first — low-cost, low-risk tests that help you calibrate before committing real resources.

For me, this looked like running simple text ads on Google for $1 a day before spending real money building out a full shoe shopping website. The ads were the bullets. The website was the cannonball.

What’s the smallest, cheapest way you can test your idea before going all in?

13. Just-in-Time Learning

A lot of people delay starting because they feel like they don’t know enough. But you don’t need to know everything upfront.

You just need to know enough to take step one, then figure out step two when you get there.

Pat Flynn’s book Lean Learning covers exactly this idea.

The most important skill for any entrepreneur is the ability to learn new skills on demand — and you get better at that by practicing just-in-time learning rather than waiting until you feel fully ready.

14. Reps, Reps, Reps

In Arnold Schwarzenegger’s book Total Recall, he talks about training to failure. For bodybuilders, failure isn’t something to fear — it’s a daily requirement for building muscle.

The same is true for most side hustles.

Honestly, it took me about 50 episodes before feeling truly comfortable behind a podcast mic. That only came from putting in the reps. You’ve got to get started before you can get good.

15. Perfection Is the Enemy of Good Enough

Growing up helping with projects around the house, my dad told my brother and I, “It’s not a piano.” And what he meant by that was it doesn’t have to be perfectly aligned.

If you bend a nail or leave a small dent in the wood, it’s not the end of the world. It’s not to say he didn’t care about quality. He cared about doing a good job, for sure.

But it was the idea that perfection is the enemy of good enough.

Reid Hoffman said it directly: “If you’re not embarrassed by the first version of your product, you launched too late.” Ship it, learn from it, and improve as you go.

16. Buy Buttons: Go Where the Cash Is Already Flowing

One of the most consistent themes across hundreds of Side Hustle Show episodes: go where the buyers already are.

The buy buttons theory is about identifying the platforms and channels where you can put your offer and make it easy for customers to do business with you — whether that’s a marketplace, a referral partner, or a platform that already has the traffic.

For services, think about who your target customers are already doing business with. Daniel DiPiazza had a tutoring business and instead of waiting for clients, he went directly to school guidance counselors with flyers about an SAT prep class.

His effective rate went from $18/hour to over $1,000 for a single session.

Carter Osborne’s college essay consulting business took off by partnering with a broader admissions consultant who didn’t want to do the essay work herself.

17. Fill Demand vs. Creating Demand

Filling existing demand is almost always easier than creating it from scratch. That’s the online equivalent of skating where the puck is going.

Practice good SEO. Use keyword research to find what people are already searching for, then build your product or content around that.

Writing articles about whatever seems interesting with no attention to search intent leads to close to zero traffic. Get in front of demand that already exists whenever you can.

18. Simplicity First, Diversification Second

As you build, it’s tempting to go in a dozen directions at once. I call this the shiny object problem and it’s especially dangerous if you’re constantly exposed to new business ideas — you hear a great one and immediately think, “why don’t I do that too?”

My advice is to master one offer, one marketing channel, and one target customer before expanding.

A recent guest, Brian Feroldi, put it well — it’s better to be excellent on one platform (he started with X/Twitter) than mediocre on ten. Get one thing working first.

19. No One Else Is Going to Do It for You

Early in my entrepreneurial journey, I noticed items sitting on my to-do list week after week. Eventually, it hit me: nobody else was going to move them forward.

The appeal and the burden of entrepreneurship are the same thing — you’re in charge.

20. Work on the Business, Not Just in It

As mentioned above, nobody else will do it for you, but that doesn’t mean you have to do everything yourself.

There’s probably plenty you don’t need to handle personally if you build a repeatable process around it.

Needing help with my shoe business led to building a whole separate site: Virtual Assistant Assistant, a VA review and directory that I ran for 9 years from 2011 to 2020.

So if you find yourself stuck in the weeds every day, try to elevate. Work on the business, not just in it.

21. Don’t Sell the Product — Sell the Transformation

Customers aren’t buying your product or service. They’re buying how it will change their life. Jacques Hopkins of Piano in 21 Days said he doesn’t sell a piano course — he sells the transformation: in three weeks, you’ll be playing your favorite songs and impressing friends at parties.

That reframe allows him to charge $500 to $1,000 for the course.

Think about the Mario mushroom: the product is the mushroom, but the transformation is you can suddenly jump higher, break through bricks, and take on bigger challenges.

What transformation does your offer really deliver?

22. LTV vs. CAC

As your business matures, you’ll start to understand what a customer is actually worth over time — their lifetime value (LTV) — versus what it costs to acquire them — their customer acquisition cost (CAC).

The profit lives in the spread between those two numbers.

William Milliken, with a pooper scooper business, said his LTV per customer could reach $3,000, because it’s a sticky, recurring service. Acquiring a customer for $100 is an easy trade.

An e-commerce example: a $35 product repurchased every six months has an LTV of $100. Acquire customers for $20, and that math works all day long.

23. If There’s a Shortcut, It’s Mentorship

You can figure everything out through trial and error. But if there’s a shortcut, it’s mentorship: tapping into the knowledge of someone who’s already walked the path.

Courses, programs, and coaches all accelerate your learning curve. It’s not cheating. It’s just a faster way to get where you’re going.

And sometimes mentorship costs nothing. Ethan Haber cold-messaged the founder of PetSmart on LinkedIn about his hamster product business.

A few weeks later, he got an unexpected call from the founder himself. Some people genuinely want to give back.

24. Opportunities Become Visible Once You’re in Motion

This felt a little woo-woo to me at first, but it keeps coming true.

The business you start isn’t usually the business you end up doing, but it gets the ball rolling.

For example, I was building a completely unrelated wine club review site when I noticed how well it ranked and how it monetized.

I had no interest in wine, but I did have interest in virtual assistants.

So I pivoted (same WordPress theme, new niche) and Virtual Assistant Assistant was born. I never would have found that opportunity sitting still.

25. Control the Controllables

“The weather in Turkey” is a phrase me and my wife used at home. It came from a trip to Istanbul where I was worried about rain in the forecast. So my wife reminded me: we’re not canceling the trip. You can bring a rain jacket.

On a related note, on my first day of self-employment after resigning from my day job, Google shut down the advertising account my shoe business depended on.

I actually went through all the stages of frustration and eventually focused on what I could control: improving the landing pages, cleaning up the site. Months later, Google reinstated the account.

You can’t stop the waves, but you can learn to surf.

26. Sharpen Your Pencil

My dad used to say: “You can’t do good work with a dull pencil.” In business, that means always looking for the 1% improvement — the small optimization, the slightly smarter or faster way to get things done.

In my shoe business days, a virtual assistant introduced me to a text expander app that completely changed how hundreds of ads were written.

And even after 13 years of podcasting, there are still small workflow improvements I find, including building mini AI agents to handle parts of the production process.

There’s always a pencil to sharpen.

27. Take Some Chips Off the Table

A lot of entrepreneurs reinvest almost everything back into the business.

In e-commerce especially, a product hits, you need more inventory, and suddenly all your capital is tied up in growth.

It’s okay to take some chips off the table.

Invest a portion of earnings into dividend-paying stocks, real estate, or other assets that work for you passively.

One example: I sold the Virtual Assistant Assistant site in 2020 when the time available to maintain it had diminished rather than watching it slowly decline.

28. If You Come to Dread the Work, It’s Time to Move On

The last thing you need is a second job you hate. There’s a fine line between pushing through the hard parts (not every day will be great) and recognizing a pattern where you genuinely dread showing up and the results still aren’t there.

Winners quit things that aren’t serving them all the time. If something isn’t working for you, it’s okay to quit, pause, or pivot.

You’re still in the driver’s seat. Business ideas are like buses; there’s always another one coming.

29. Celebrate Your Wins and Progress Daily

Entrepreneurship can be a lonely road. Nobody else knows what you’re going through, so you have to take stock yourself.

A simple nightly practice makes a big difference:

What did I get done today?
What am I grateful for?
What are my top priorities for tomorrow?

That’s the foundation of my 3 Question Journal.

John Lee Dumas gave me the line: “You win tomorrow today.”

Knowing exactly what you’ll work on first (before reacting to anyone else’s agenda) keeps you moving forward intentionally. Give yourself permission to celebrate the small wins along the way.

30. The Journey Is the Destination

The goal matters. Set the GPS. But the destination isn’t where the real life happens… the journey is.

The recipe for happiness = meaningful work + meaningful relationships + a sense of progress.

Joe Saul-Sehy from Stacking Benjamins puts it well: he’s embarrassed by the work he did a year ago and hopes to be embarrassed by today’s work a year from now. That’s the journey.

Find work that matters to you, build relationships along the way, track your progress, and enjoy it.

Episode Links

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