u/BobbyBizScout

5 years ago today, I signed a deal for my (then) employer that lost my company millions of dollars.

I was running marketplace at SeatGeek. The deal was a multi-year partnerships with the Wells Fargo Center.

Everyone at the company told me not to sign it. I signed it anyway.

Wells Fargo Center (now Xfinity Mobile Arena) was one of the biggest venues in the country for concerts and events. I was sure it would work.

Then the Flyers started playing.

Year 1:
46 losses out of 82 games. They set a franchise record with a 13-game winless streak. The arena was empty. The events they were booking weren't any better. Third tier shows and boxing matches nobody had heard of. We lost over a million.

Year 2:
Finished 7th in their own division. 29th out of 32 teams in goals scored. UBS Arena opened in New York and was blamed for pulling concerts away from Philadelphia. Still couldn't make the playoffs. We lost over a million again.

Year 3:
Thought we could turn it around. The Flyers held a playoff spot for 4 months. Then they went 0-6 in their last 8 games and collapsed out of contention. Another million plus gone.

We were still profitable due to customer acquisition, and we had the stickiest product in ticketing. We made up for it over the long haul. But cash out the door looked bad. And I never heard the end of it.

When we signed the deal the Flyers sent me a custom jersey. SeatGeek on the front, number 21 on the back. Now I look back on it as the jersey that cost me somewhere around $4M in cash.

The amount of babysitting of other people’s feelings that comes with it.

So much energy and time gets lost managing how people receive feedback. You have to constantly calibrate how direct you can be or else someone might spiral if you push too hard.

I'm not an a**hole and I'd never want to have one on my team. I still interview every new hire myself (partly for that reason). But there are moments where I'd just want to say what I'm actually thinking and move on without having to sugarcoat it to protect someone’s feelings.

If I ever retire, it’ll be because the politics of work got the better of me.

How you can take advantage of it to buy a boring cash-flowing business in 2026:

An SBA loan lets you borrow money to buy a business. Because the government backs it, banks offer terms you can't get anywhere else: Low down payment and long repayment window.

Up until now, the maximum you could borrow was $5 million. Starting July 4th, borrowers can combine:

• SBA 7(a): up to $5M (acquisitions, working capital, debt refinancing)
• SBA 504: up to $5M (real estate & equipment)

Stack both and you get $10M in gov-backed financing for a single deal, which means you're targeting businesses doing $800k-$1.5M/year.

How to position yourself to close one:

Step #1: Get your financials in order

Pull your last 2-3 years of personal tax returns an get your credit above 680. Lenders need to see your financial history before they underwrite. The earlier you pull it together, the faster you move when you find the right deal.

Step #2: Find a business

Look for businesses doing $150k-$500k in SDE. That's where SBA financing is most powerful & competition from PE is lowest.

Step #3: Get an independent valuation

Lenders need proof the business is worth what you're borrowing for it. An independent valuation answers that and tells you whether you're overpaying. Hire a CPA and an M&A attorney.

Step #4: Submit the LOI

This lays out the price and basic deal terms on paper. It's not the final contract, but it shows the seller you're serious and gives lenders the deal structure they need to start underwriting. Without it, you don't get the loan.

Step #5: Get seller financing

The SBA requires 10% down for full ownership. A seller note can cover half of that. So on a $1M deal, the seller can fund $50k, you bring $50k, and the loan covers $900k. You own a $1M cash-flowing business for $50k out of pocket.

I understand that because I've felt it myself.

I grew up in Stockton, California. Nobody in my world bought businesses. That entire ecosystem felt like it belonged to people with much more resources and connections than I had.

But the numbers tell a different story.

I now run a marketplace for business listings. Here’s what the data shows:

• 22% of businesses listed under $100K
• 45% under $200K
• 43% under $250K

For context, the average home in the US right now costs $435k.

That means you can buy a profitable business with customers and employees for less than the price of an average home. And that's before you even factor in the financing options.

With an SBA 7(a) loan, you only need 10% upfront. The government backs the rest. The seller can also fund half your down payment through a seller note, meaning they loan you that amount back and get repaid over time as part of the deal.

So on a $250k deal:

• The SBA loan covers 90% ($225k total)
• You’re left with 10% ($25k)
• The seller funds half that through a seller note ($12.5k)
• You bring the remaining $12.5k cash

You bought a cash flowing asset worth $250k for less than the price of a used car.

1. Connect Claude to your QuickBooks and PayPal. It pulls your cash position, checks what's still outstanding, cross-references incoming settlements, and builds a 30-day cash forecast in one run. Then it ranks which invoices are overdue and queues the follow-ups for you to approve.

2. Before you sign anything, it reviews contracts and flags what you need to know: bad termination clauses, automatic renewals, liability exposure. Connect DocuSign and it handles the outbound too: sends for signature, tracks status, and files the executed copy when it comes back.

3. Plug in HubSpot and Canva. It ranks incoming leads by likelihood to close, finds the slow periods in your revenue, drafts a campaign strategy around them, and generates the assets in Canva ready to go live.

It’s one of the most useful things I've seen come out of the AI space for SMB owners. This is just scratching the surface.

Will post updates as I find more.

I hired more than 50 people. Only found 2 who actually cared.

First was a mother with 5 kids. Started as a minimum wage cook. Had 2 more kids while working for me. Back in a month both times (I told her to take more time off and I would continue to pay her but she wanted to work). Eventually promoted her to assistant manager.

Second was a high school kid running front of house better than most adults I've managed. Then she left for college.

That’s 2 out of 50+.

Good luck building a business on those odds.

None of them offered much (if any) when I was hired... I had to go get it.

I would go to my boss, and tie the ask to a number: "If I grow revenue 50% in the next 12 months, is a 10% ownership stake on the table?" That would turn the ask into a deal. Owners are a lot more receptive to that than you just asking for equity.

They might not say yes on the spot. But now you’ve started a conversation. And that conversation often turns into a negotiation. Most people never ask because they assume their boss will say no. Ask anyway. Worst that can happen is you stay where you already are.

You guys are at the start of your journeys... which hopefully means you can learn from my errors, and NOT lose millions of dollars on bad business deals.

Genuinely, avoid these:

1. Don't do business with friends

You can do business with people you like. But if you're actually friends outside of work, don't put a business in the middle of it. A friendship is worth more than any deal, and deals have a way of ending friendships.

2. Never go 50/50 on a partnership

It looks fair on paper. It isn't. One divorce and your partner's ex owns half your company. One disagreement on a major call and you're deadlocked, so it's stalemate or lawsuit, take your pick. Make it 49/51, or don't do it at all.

3. If it's family, write everything down

What happens if someone dies? If someone wants out? If you disagree and neither side backs down? People assume family makes these conversations unnecessary. That assumption is exactly how most family businesses fall apart.

4. Never be the smartest person in the room

Someone around you should always know more than you about something. If nobody does, you've messed up somewhere. Either you hired wrong, or you've surrounded yourself with people who won't push back. Both quietly kill your growth and the company's.

5. Don't work with people you don't like

You'll spend more time with your business partners and employees than with your own family. If the thought of sitting across from someone in a meeting makes you tense, that's your answer. Life's too short and the work is too hard to add that on top.

They hear the word and assume they're buying themselves a job. Or that the franchisor takes all the upside and leaves you with the scraps. But that’s not true.

I’ve ran two franchise stores myself. Every good one wants the operator to win.

• They turn down more applicants than they let in.
McDonald's approves fewer than 5% of applicants, Chick-fil-A less than 1%. They have quality filters to protect the model so you don’t get screwed.

• They tell you exactly where your numbers need to be.
Revenue per location, labor as a percentage of sales, food cost targets, margin floors, etc. so you’re never left guessing.

• They've already negotiated your supplier relationships for you.
You'll never find yourself negotiating with vendors like you would running your own business.

Building that kind of clarity from scratch as an independent owner takes years.... if you even get there. That's worth something.

Most people assume you need $500k in the bank before you can buy a business and start making money from it, but honestly you don't. I would know, I've bought several (with far less than 500K in my bank account).

You need to understand how two tools work. I've used both, so here's the plain-English version.

Tool #1: The SBA 7(a) Loan

This is a government-backed loan. The SBA guarantees up to 85% of it, which makes banks willing to fund deals they'd normally pass on. You can borrow up to $5M and repay over 10 years. For buying a business, you can put as little as 10% down. So on a $1M deal, the loan covers $900k and you bring $100k to the table.

Tool #2: Seller Financing

This is where the seller acts as your bank for part of the price. Instead of getting all their money at close, they collect a chunk over time, with interest, written right into the purchase agreement.

Sellers actually like this for a few reasons. Spreading the income over multiple years can lower their tax bill. Deals with seller financing tend to close faster and at higher prices. And a seller who's still owed money has real skin in the game after you take over.

Plus, you can stack them.

The SBA lets seller financing count toward your required down payment. The seller note goes on "full standby" (meaning they don't get paid on it until the SBA loan is done) and it can cover up to half of what you're required to put in.

So on that same $1M deal, the math can look like this:

• SBA loan: $900k (90%)
• Seller standby note: $50k (5%), on standby for the life of the loan
• Your actual cash at close: $50k (5%)

The business itself generates the cash flow that pays down the debt. You own it from day one.

For scale: the SBA backed over $37 billion in 7(a) loans in fiscal 2025, and a big chunk of that went to acquisitions structured pretty much exactly like this.

The barrier isn't money, it's knowing the tools exist. Happy to answer questions in the comments.

A question I've been sitting with lately:

Is there such a thing as an irreplaceable employee, and what do you do if someone like that leaves?

For most of my career it was never my problem to solve. I spent most of my career working for some of the biggest companies in the country. When a key person would leave they’d just absorb it and move on. But now as a leader of a 30 person startup it’s an interesting thing to think about.

I don't have an answer yet.

You all are way ahead of where I was at your age, so figured I'd share what I wish someone told me.

I did the "responsible" thing. Got the corporate job, chased promotions for 15+ years. Took me almost that whole time to realize a salary is kind of a trap. You get taxed before you even see the money, and the second you stop showing up it ends. You're not building anything that keeps paying you.

What actually changed my net worth was becoming an owner. My brothers and I started buying small, boring businesses on the side while I still had my day job. Got to four of them running in the background before I quit corporate for good.

A few things that blew my mind once I learned them, and that I wish I'd known at 22:

You don't need to be rich to buy a business. In the US, SBA loans can be as little as 10% down. That means a $500k business might only need around $50k to acquire. There's almost nothing else a normal person can buy with that kind of leverage.

The business pays back its own loan. Lenders want it generating about $1.25 for every $1 of debt payment before they'll approve it, so the company's own cash flow is what builds your equity, not your paycheck.

They're shockingly cheap. Stocks trade at like 20-25x earnings. A small main street business goes for 2-5x. A business making $200k/yr might cost around $700k. That same income through an index fund would run you $4M+.

It's not passive (ignore anyone who says it is), but a good one comes with staff and systems, so it keeps earning while you're doing other things. You manage it, you don't run it day to day.

I'm not saying drop everything and go buy a laundromat tomorrow. But if I could go back, I'd have spent way less energy climbing a ladder and more energy learning how to own things. You've got the biggest advantage there is, which is time. Use it.

Happy to answer questions about SBA loans or how we find and screen deals if anyone's curious.

In my experience, this is a terrible reason to buy a business. But curious your thoughts.

Typically, you'll end up under researching, overpaying, and taking the first halfway decent deal you can find just because you want out fast.

Keep your W2. Buy the business. Then run both until the business is making enough to replace your salary.

That takes at least a year in most cases.

If I didn’t have my full time job when my 2 restaurants failed I would’ve lost my house. Your salary is your safety net.

Will you?

I say this as someone with an MBA from one of the top finance schools in the world. College was the greatest time of my life. I loved every second of it.

But I can't name a single thing I learned in four years of undergrad that made me better at my job.

Even seven years ago at SeatGeek, we hired any high school graduate who could code well enough to pass our tests. No degree required.

By the time my kids turn 18, the only reason to go to college will be a government regulation requiring a degree to enter a specific field. If they're talented enough to play NCAA sports, different conversation.

Other than that... hard pass.

I'd rather save them $200k in debt for a degree built for a world that doesn't exist anymore.