Here’s our latest interview with a side hustler!
It’s been awhile since we’ve had one, so sit back and enjoy!
As you know, I love creating a side hustle as part of a fast-track path to financial independence because it can make a huge difference (see this financial calculator), enough to actually get you to FI in 10 years.
If you have a side hustle and would like to be interviewed, shoot me an email and we can talk over specifics.
This interview was submitted in July.
As usual, my questions are in bold italics and their responses follow in black.
Here we go…
GENERAL OVERVIEW
How old are you (and spouse if applicable, plus how long you’ve been married)?
I’m 41 years old and single.
It’s me and my three kids, and they are the entire reason this side hustle exists.
Do you have kids/family (if so, how old are they)?
Three kids, a boy and two girls, ages 6, 8, and 11. All three are named after songs by my favorite band, which tells you most of what you need to know about how I make decisions.
They function as my board of directors. Every business choice runs through one filter: does this get us closer to the life I want to give them? And that life is very specific.
It’s a house with a kitchen island and a built-in griddle for Saturday morning pancakes, and someday, a backyard lazy river. That’s the whole mission statement.
What area of the country do you live in (and urban or rural)?
Southern California, in the Inland Empire east of Los Angeles. Suburban, which happens to be pool country.
There are more private backyard pools within an hour of my house than almost anywhere else in America, and most of them sit empty most of the time. That detail becomes important shortly.
What is your side hustle?
I run Pool Rental Near Me, a peer-to-peer marketplace where families rent private backyard swimming pools by the hour, the same way Airbnb lets you rent someone’s house. Pool owners list their pool, set an hourly rate, and keep the large majority of every booking.
Families get a private pool for a birthday party or a hot Saturday afternoon without the cost of owning one. I make my money on the transaction in the middle.
As of this writing there are 93 pools live on the platform, the median host earns about $48 per hour when their pool is booked, and our largest single booking so far was $825.
I built all of it from the sleeper cab of a semi truck, and I’m competing directly with a venture-funded incumbent that has raised tens of millions of dollars. I have raised zero.
Is there anything else we should know about you?
My day job is driving a semi for a traveling carnival, paid by the mile — $1,500 a week guaranteed, and more in a strong week when I’m turning around 3,000 miles. But the carnival runs on a season, February through October, which becomes important later.
I grew up around the carnival business through family and spent roughly twenty years in and around it. Everything I understand about this side hustle traces back to the midway, and I’ll explain exactly how in a minute.
CREATION STAGE
Is this your first side hustle? If not, could you give us a bit of background on past efforts — both successes and failures?
Not the first, and the one right before this was the most instructive failure of my life: a website renting out ferris wheels. The demand was real, and the phone rang constantly.
We closed two bookings, one for $14,000 and one for $16,000. The business died anyway, because there were only about twenty ferris wheels in all of California, I didn’t own any of them, and on the third deal the wheel’s owner simply cut us out and dealt with the customer directly.
Demand was never the problem. Supply was. So when I found pool rentals, I recognized it instantly as the same ticket-box model with the supply problem flipped upside down: instead of twenty ferris wheels, there are millions of backyard pools sitting idle.
Before the ferris wheels there was always something, whether it was selling on eBay and Amazon or buying liquidation pallets to flip. I’ve never not had a side hustle.
This is just the first one that could ride in the truck with me. Along the way I also self-published seven books on pool hosting.
None of the early efforts made meaningful money on their own, but every one taught me something I use daily now. The books became my authority engine, because it turns out ‘published author on the subject’ opens doors that ‘guy with a website’ does not.
I stopped calling any of them failures a while ago. They were the cost of the education, and it was cheaper than college.
How did the idea of starting a side hustle begin?
A seasonal paycheck started it. I drive for a traveling carnival, and I’m paid well by the mile, but the season runs February through October.
Come November, the routes stop and so does the money, every single year. I don’t have a job with a ceiling. I have a job with an off-season.
Nine months of driving and three months of watching the account drain, on repeat, and you cannot raise three kids on an income that clocks out for a quarter of the year and just hope it works.
The paycheck was never too small. It was too fragile. It stops the moment I stop driving, and once a year the calendar guarantees I stop.
What driving does give you, though, is time to think. A long day alone in a cab is a paid strategy retreat if you decide to use it that way.
Somewhere on I-10 I decided I was done trading hours for dollars with nothing compounding underneath me, and that whatever I built had to keep paying whether I was driving or not, and no matter what month it happened to be.
How did you come up with the idea?
The idea itself came straight from the carnival. Twenty years around the midway teaches you one lesson on repeat: the ride owners carry all the assets, the maintenance, the insurance, and the headaches, while the ticket box quietly takes a cut of everything that moves.
Whoever owns the transaction owns the business. I never forgot that.
So when I learned that people were renting out their backyard pools by the hour, my reaction was not ‘I should get a pool.’ It was ‘somebody needs to own the ticket box for this.’
I had several ideas on the list at the time, including other software products, but I ran them all through the same test: is there proven demand, and is anyone serving it badly? Then I looked at the search data.
The phrase ‘pool rental near me’ was being typed into Google constantly, in enormous volume, and the companies in the space were doing a surprisingly poor job of showing up for it. Massive visible demand plus weak distribution from the incumbents.
That was the only idea on my list where the opening was sitting in plain sight, so I picked it.
What made you think this particular idea could be profitable?
Three reasons. First, marketplace unit economics are beautiful for a broke founder: I own no pools, clean no filters, and carry no inventory, yet I earn a percentage of every booking that crosses the platform.
Hosts charge roughly $45 to $75 an hour, so even a modest cut of each booking is real money, and it scales without me buying anything. Second, the market was already proven at someone else’s expense.
A venture-backed competitor had raised tens of millions of dollars doing exactly this, which meant I never had to wonder whether strangers would rent another family’s pool. They would, by the millions.
Third, and this is the part most people miss, that same competitor was steadily raising fees on its own pool owners and generally treating its supply side like a captive audience. When an incumbent starts squeezing the very people who make the product exist, it opens the door for a host-first alternative.
I didn’t need to beat them everywhere or outspend them anywhere. I needed to be the obviously better deal for the pool owner, and let the pool owners do the talking.
What were the early days like — getting your side hustle off the ground, making your first dollar, etc.?
Brutal and fun in roughly equal measure. I built the first version at truck stops between midnight and 5 a.m. using off-the-shelf marketplace software, because I’m not a classically trained developer and I couldn’t afford to hire one.
I recruited the first pool owners one at a time, by hand, explaining to each of them why they should trust a truck driver with their backyard. The objection was always the same, and it was fair: what happens if something goes wrong?
So I answered it with infrastructure instead of promises. Liability protection, digital waivers signed before anyone gets wet, house rules baked into every booking, and free training so hosts knew exactly how to run a safe, professional operation.
Trust is not a vibe, it’s a checklist, and building that checklist is what turned skeptical homeowners into my founding hosts. My first booking tells the whole story.
I’d run two $8 test bookings on myself in November 2024 just to prove the plumbing worked, but the first real one landed on the Fourth of July, 2025: $181.50 for an Independence Day swim, from a total stranger who found us, trusted us, and paid. I sat in the cab staring at my phone thinking an unprintable version of ‘holy hell, this actually works.’
Then came my favorite plot twist of the whole journey. Early on I launched under a different name, and the venture-funded incumbent sent me a cease-and-desist letter over it.
Picture that for a second: a truck driver with three kids getting legal mail from a company with tens of millions in funding. I rebranded. And in the process I noticed something interesting.
That same company was buying Google ads on the exact phrase ‘pool rental near me.’ They were spending real money to show up for those exact words.
Their own ad budget told me precisely which digital real estate mattered most, so I acquired the exact-match domain and rebuilt the entire brand around it. Their legal letter forced the move and their ad spend drew me the map. I’ve been oddly grateful for that letter ever since.
BUILDING STAGE
What did you do to grow your side hustle? Were there any specific actions that resulted in major breakthroughs?
One strategy mattered above everything else: programmatic SEO. I could not afford ads, so I built thousands of genuinely useful pages targeting every city and every situation people actually search for, things like pool rentals in a specific town, birthday party pool rentals, kids’ swim safety guides, and hosting guides for pool owners.
The compounding took time and then it didn’t. In March 2025 the site was getting about 80 search impressions a day.
Twelve months later it was over 39,000 impressions a month, roughly a sixteen-times year-over-year jump, and in one recent 28-day stretch we passed 4,000 clicks from Google.
In several major metros, including Phoenix, Dallas, Las Vegas, and Orlando, my pages now outrank the venture-funded incumbent in organic search. The second breakthrough was positioning: I went all-in on being host-first.
Lower fees than the incumbent, locked-in founding rates for the earliest pool owners, and a mountain of free value on top, including free pool host courses that have grown into a 142-course academy, the seven published books, and more than fifty free tools like waiver generators and earnings calculators.
The third breakthrough isn’t a tactic, it’s a habit: speed. When a founding host reported a notification bug, I diagnosed it and shipped the fix in 27 minutes, from the road.
A funded competitor cannot buy that. Pool owners talk to each other, and ‘the founder personally fixed my problem in under half an hour’ is the kind of sentence that recruits the next ten hosts for free.
What ties all three together is the marketplace flywheel: the pages bring renters, renters create bookings, bookings prove to pool owners that real money is on the table, new pools give me more inventory and more pages to build, and the loop feeds itself.
My job is to keep every stage of that loop unclogged. One small example of how deep the SEO work goes: when I built out Spanish-language pages for my Southern California markets, I went back and rewrote hundreds of them into the regional dialect local families actually use, because ranking for the textbook word nobody types is the same as not ranking at all.
Nobody sees that work. Google does.
What sort of time commitment did your side hustle require while becoming established?
About thirty hours a week at a minimum during the season when I’m on the road, and closer to sixty a week in the off-season when I’m home.
The honest answer is that it’s daily. The cab is my office. I strategize and dictate work on the road, then build hands-on when I’m parked, and AI tools mean the business travels with me, so there is no version of my week where it isn’t getting hours.
Nearly all of it lands late at night or on weekends. During the big site builds it was effectively a second full-time job stacked on top of the first one. I won’t pretend it was balanced. It wasn’t. It was a deliberate, time-boxed sprint to buy my family a different future.
Where did you find the time to work on it?
Two places. The driving season itself is secretly full of dead time: mandatory rest breaks, waiting to load and unload, nights in the sleeper.
Most drivers fill that time with TV and scrolling. I filled it with building. Then there’s the off-season.
Those same three winter months that scare me financially are the reason the business exists, because November through January is when my thirty hours a week on the road becomes sixty at home. The off-season is a threat and a gift at the same time.
And the rest of the honest answer is that I traded sleep. When the kids were down, that was my shift.
I treated 2 a.m. the way other people treat 9 a.m., and I built a business in the hours everyone else agrees don’t count.
Were you the only one involved or did others help out?
Mostly me, but not only me, and the exceptions matter. A partner handles day-to-day host outreach and relationships as my COO, which freed me to focus on building.
A passive investor holds ten percent of the company in exchange for covering the core marketplace software subscription, which was precisely the bill I could not afford in the early days, so that trade bought the company’s survival. And I’ll say the quiet part out loud: I lean heavily on AI tools for code, content, and strategy.
AI is how one driver ships work that used to require a funded team of specialists. It is the great equalizer for solo founders right now, and anyone starting a side hustle in 2026 without using it is leaving their single biggest advantage on the table.
RESULTS
Can you give us specifics on what you earn with your side hustle?
Here are the real numbers, pulled straight from the ledger, because vague ‘six figures’ hand-waving drives me crazy and I promised the editor none of it.
Since launch, pool owners on the platform have grossed $7,321 in total bookings across 36 paid bookings, and $6,645 of that came in the trailing twelve months. Of that gross, the hosts kept $6,194, which means about 85 cents of every dollar a guest spent went straight to the pool owner.
Our biggest single booking so far was $825, and the median host earns about $48 an hour when their pool is booked. My revenue is the platform’s share of each booking, and all-time that share has come to $1,127, which works out to under $100 a month right now.
On top of the marketplace I run a few small side products that grew out of it, including a pay-per-use digital waiver tool, a low-cost direct booking tool for pool owners, and royalties from the seven books. Together they add a trickle, not a river, and they do not meaningfully change the picture.
So let me be completely straight with your readers about what these numbers mean: I am the before picture, not the after picture. The revenue is real but small, and in a marketplace, revenue is a lagging indicator.
The leading indicators are pools listed, search traffic, and host loyalty, and all three are pointed the right way.
On the fee side, since that is how the revenue gets generated: our standard structure is a 10% host fee plus a 10% guest booking fee, and we cover the payment processing costs ourselves. For 2026 we are running a promotional 0% host fee with just a 5% guest fee, which has turned out to be our single best host-recruiting tool.
Pool owners pay nothing until a guest actually books, and there is no membership or monthly cost to list, ever. Whether the 0% promotion extends into 2027 is a call I will make at the end of the summer once I see how the season shakes out.
Costs run about $350 a month out of my own pocket, roughly $92 for servers, $200 for AI tools, $30 for text messaging, and the rest in small API and software charges, or about $4,200 for the year. The core marketplace subscription of $400 a month is covered by my investor, as described earlier.
Put it all together and here is the honest bottom line: fully loaded, this business runs at a deliberate monthly loss that I subsidize with my driving income. That is not an accident and it is not a failure. It is the plan.
My paycheck funds the company, which is exactly what lets me offer a 0% host fee while the funded incumbent raises theirs. I am buying the supply side and the search traffic now, with patience instead of venture capital, and I will turn on profit later.
I am the before picture, not the after picture, and I would rather show you a true loss than a padded win. The traffic, the pools, and the brand are the real balance sheet, and none of them show up on a profit-and-loss statement yet.
What impact has this extra income had on your finances?
So far it hasn’t changed my family’s month-to-month finances at all, because I reinvest every dollar the business makes back into infrastructure and technology, including a full redesign of the site around what customers actually need. I have not brought home a dime, and that is deliberate.
My goal right now isn’t to take money out; it’s to make the platform undeniable, which is the whole reason I can run a 0% host fee in the first place. What it has changed is our trajectory and my optionality.
I now own an appreciating asset instead of only a paycheck. If I stopped building today, the platform, the content library, and the domain hold real value that did not exist two years ago, and nobody can lay me off from it.
There’s also an impact that never shows up on a spreadsheet: my kids are watching their dad build something instead of only watching him leave for work. Ask me in a few years which of those mattered more.
What went well in this process?
The SEO bet paid off bigger than I hoped, and it compounds while I sleep, which was the entire point of choosing it. The host-first positioning worked exactly as designed; pool owners can tell when a platform genuinely respects them, and they reward it with loyalty, referrals, and patience when things break.
Bootstrapping kept me honest. With zero dollars raised, every decision is fast, every dollar has a job, and no investor can ever force me to squeeze my hosts to hit a growth target.
And betting on my own strange background paid off. The carnival taught me the ticket box, trucking gave me the hours, and being broke made me resourceful.
It turns out the resume I thought disqualified me was the edge. And the hosts themselves went well, which sounds obvious but isn’t.
Several founding hosts have grown into genuine operators, building out full party packages, add-on menus, and repeat customer bases around their pools, and a few have become informal ambassadors who recruit other pool owners in their area without being asked. When your supply side starts selling for you, you know the positioning landed.
What could have gone better?
Plenty. The naming mistake cost me a legal scare, a forced rebrand, and months of lost brand equity, and a $300 trademark search on day one would have prevented every bit of it.
I also chased too many side products before the core marketplace was fully humming. Every one of them is useful today, but building two or three of them early was distraction dressed up as productivity.
And my two structural weaknesses are ones I still actively work on: too much of the business runs through me personally, and too much of my traffic comes from a single source, Google. Concentration is a gift on the way up and a threat the entire way through, and I don’t get to pretend otherwise just because it’s currently working.
What do you wish you would have done differently?
I would have bought the exact-match domain and done trademark diligence on day one instead of learning that lesson by certified mail. I would have started collecting email addresses in the first week, because an audience you own is the only traffic no algorithm update can take away from you.
And I would have narrowed my focus about a year sooner than I did. The single biggest jump in my results came the day I ruthlessly stack-ranked everything: core marketplace revenue and traffic first, and everything else waits its turn.
Focus was the feature I shipped last, and it should have been first.
Has it been worth it? Why or why not?
Yes, and I won’t romanticize the price tag. It has cost me sleep, social life, and a few years of nights that I will not get back.
But weigh the alternative. The alternative was a seasonal paycheck with a three-month hole in it every single year, and hope as a retirement plan.
Building this gave me leverage, rare skills, a real asset, and a genuine shot at a categorically different life for three kids. And even in the worst case, where the whole thing fails tomorrow, the person it forced me to become can build the next one twice as fast.
The business is the first prize. The builder is the second one, and nobody can repossess him.
What are your future plans for your side hustle?
Near term: keep stacking pools and search traffic, get the mobile app fully under my own control, and grow platform revenue to the point where it replaces my seasonal driving income entirely, so I can come off the road and run this year-round.
Medium term: expand the host-first model into more metros where the incumbent is weakest, and keep turning the free tools and academy into the industry’s default education layer.
Long term, the plan is simple, and I’ve already put it in writing to the editor of this site: the day this business crosses seven figures, ESI Money gets the millionaire interview first. Consider this article part one of a two-part series with a few years between episodes.
What advice do you have for ESI Money readers who may be thinking about creating their own side hustle?
First, own the transaction, not the asset. The ticket box beats the Ferris wheel every time.
Look for places where money is already moving and position yourself in the middle of it instead of buying the inventory.
Second, pick a fight where the incumbent is mistreating its supply side. You do not have to outspend a funded competitor; you have to out-care them with the people who create the product, and those people will become your sales force.
Third, distribution beats perfection. I shipped an imperfect site and poured my energy into search traffic instead, and that compounding traffic is now the moat.
Fourth, you do not need capital, you need consecutive nights. I built this at truck stops with a laptop, off-the-shelf marketplace software, and AI tools.
The toolset available to a broke solo founder in 2026 is genuinely absurd, and it gets better monthly.
Fifth, audit your dead time. Everyone has a version of my sleeper cab, whether it’s a commute, a lunch hour, or the two quiet hours after the kids go down.
That time is either compounding into your future or it’s evaporating, and it never asks which you chose.
Sixth, document everything you learn as you learn it, because your education is a second product. Every hard lesson from building this business became a book chapter, a course, or a free tool, and that library now does my marketing, builds my authority, and earns royalties while I drive.
Most people learn expensive lessons and let them evaporate. Write yours down and they pay you twice.
And one last piece specifically for this audience: a lot of ESI readers are sitting on a pool that does nothing but cost money most of the year. That pool is an income-producing asset in disguise.
The median host on my platform earns about $48 an hour from theirs, and if you’re curious what it actually takes, I wrote the full playbook on renting out your pool and put it up for free.
But even if you never list a pool anywhere, the underlying lesson holds for everyone reading a site like this one: an asset you already own, plus a marketplace that respects you, is the easiest side hustle math in the world. Find yours.
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