So Build It Anyway: Growing an Online Business from a Secondary Market

The last two things I wrote here were diagnoses. One about San Antonio itself and why building a startup here is harder than the boosters admit. One about Geekdom, the building most founders here walk into first.

Both got read more than I expected, and they produced the same message in my inbox over and over. Some version of: okay, so what do I do?

Because here’s the thing about the advice everyone gives. “Move to Austin” assumes you can. The people writing to me have a house here. Kids in a school they like. A spouse with a job. Parents twenty minutes away who are getting older. Picking up and leaving isn’t a strategy for them; it’s a fantasy someone else can afford.

So this is the other post. Not what’s wrong with the ecosystem, but what to actually build when you’re staying.

My qualifications are mixed, which I think makes them more useful. I built and exited a startup. I run Ruskin Consulting, a seven-figure agency managing over $10 million in annual ad spend. Through Hitchens Ventures I invest in and advise founders around Texas, and I mentor through Geekdom, 1 Million Cups, and VentureLab. I also spent years betting on a version of this ecosystem that turned out not to exist, so I’ve paid for a few of these lessons directly.

Build boring software for the industry outside your window

Here’s the pattern nobody puts on a panel. The two biggest software outcomes San Antonio has produced weren’t tech companies. They were software companies pointed at industries that couldn’t care less about software.

XPEL sells paint protection film for cars. It was founded here in 1997, it’s headquartered on Broadway downtown, and it trades on the Nasdaq, doing close to half a billion a year. Deeply unglamorous business. But the thing that makes XPEL defensible isn’t the film, it’s DAP. That stands for the Design Access Program, a proprietary database of vehicle patterns that installers use to cut film for a specific year, make, and model. An installer logs in, picks the car in front of them, and the plotter cuts the exact shapes needed. Without it you’re trimming by hand and hoping. Installers don’t just buy film from XPEL; they buy access to the patterns, which is why they don’t leave. The software was never the product. It was the switching cost.

ParLevel built management software for vending machines. Two guys who met at a Three Day Startup weekend at Geekdom, took $25,000 from the community fund and raised roughly $2 million total. They sold to 365 Retail Markets for a number reported in the tens of millions. The acquirer wasn’t a tech company. It was a vending industry company that needed what they’d built.

Both are SaaS. They just don’t look like the SaaS on your feed, because the customer isn’t a startup and the buyer isn’t a VC.

So look out your window. This is what’s actually here:

Sector	Scale in San Antonio	Where the software gap usually sits
Defense and military	roughly $53 billion in annual activity	subcontractor compliance, clearance tracking, bid and proposal workflow
Healthcare and biosciences	South Texas Medical Center at roughly $18 billion	scheduling, prior auth, patient intake, referral routing
Cybersecurity	one of the largest concentrations in the country	vendor risk, audit evidence collection, client reporting
Logistics and trade	I-35 corridor and cross-border freight	carrier onboarding, customs docs, yard and dock coordination
Food, retail and hospitality	H-E-B, plus a huge independent restaurant base	inventory, scheduling, supplier ordering, compliance logs

Every one of those runs on spreadsheets and phone calls somewhere. You will never out-execute a Bay Area team on a general-purpose developer tool. You can absolutely be the only person in America who understands how a mid-size defense subcontractor handles compliance paperwork.

Lean into the thing you’re already obsessed with

The reason I can raise money for AdLlama isn’t that I have a better deck than someone in Palo Alto. It’s that I’ve run paid media for over a decade, I manage more than $10 million a year in ad spend, I own an agency, and my phone is full of other agency owners.

So when I talk about what an agency owner needs from an AI ads tool, I’m not theorizing. I am the customer. I know what the workflow actually looks like at 4pm on a Thursday when a client is unhappy. I know which parts of the job people would pay to never do again. And I can get twenty agency owners on the phone this week because I already know them.

That’s an unfair advantage, and it’s the only kind that survives a market where you can’t outspend anybody. Ask yourself:

• What industry have I already spent five or ten years inside?
• What do I know about how it really works that an outsider would need two years to learn?
• Whose phone number do I have that a stranger would need six months to get?
• What do I find myself explaining over and over because nobody else seems to get it?

Wherever those four answers overlap, that’s your company. Not the idea you thought of in the shower, the one you’re already qualified to build faster than anyone else. In a market with no capital advantage and no talent glut, domain obsession is the only edge that compounds.

Raise money by asking for everything except money

Founders here assume raising means booking a flight and pitching a room full of strangers. Half of that is right. You will take flights. But the pitching part is where most people get it wrong, and it’s why so many come home empty.

At preseed and seed, almost nobody writes a check off a cold pitch. They write checks into people they’ve already been talking to for months. So stop pitching and start doing the thing that works, which is asking for input.

• Ask them to poke holes in your pricing. You get free consulting.
• Ask what they’d need to see before this was investable. You get their actual criteria, in writing.
• Ask who else you should be talking to. You get the introduction, which is the whole game.
• Ask what they’d be worried about if they were you. You find out the objection before it kills a real conversation.

Those requests do something a pitch can’t. They make the person feel useful instead of sold to. Money tends to arrive later, sideways, from someone in that chain. The old line is that if you ask for money you get advice, and if you ask for advice you get money. It’s a cliche because it keeps being true.

But none of it works without the part everybody skips. You need customers. Real ones, paying real money, who will get on a call and say they’d be annoyed if your product disappeared. Every conversation above goes better when you can open with what people already pay you. Traction is the only thing that makes a secondary market address stop being a question. Get twenty customers before you go get a term sheet, and the term sheet meeting becomes a completely different meeting.

Your weapon isn’t low burn; it’s a longer payback period

Everyone tells founders in cheap cities that low burn is their advantage. True, and also passive. Here’s the active version.

You and a funded competitor both want the same customer. Their board wants customer acquisition cost paid back in six months, because that’s the number that makes the next round look good. Yours can take eighteen, because you’re not raising and your costs are half theirs.

Run the math on a customer paying $200 a month. Their 6-month window lets them spend about $1,200 to win that customer. Your 18-month window lets you spend about $3,600.

You can rationally pay three times what they can for the exact same person and still be the healthier business. In an auction, whoever can pay the most usually wins. Most founders in your position never realize they’re the one who can.

Know your payback period cold. Estimate theirs from their funding stage and pricing. Then bid like someone who intends to keep the customer for four years, because you do.

Own a channel before you need one

There’s no bridge round waiting for you locally. I made that case at length already and won’t repeat it. The practical consequence is worth stating plainly though: you need something that produces customers on demand and doesn’t require permission or capital to switch on.

I’ll go further than that. Founder-led marketing is the single best thing you can do for a business right now, and it’s not close.

The market has moved decisively toward people rather than logos. The creator economy was valued at roughly $250 billion globally in 2025, with credible forecasts putting it north of a trillion by the early 2030s. Influencer marketing alone is expected to hit about $32.5 billion in 2025, up 35.6% in a single year, and the IAB found that 48% of creator-ad buyers now treat creators as a must-buy line item. The most telling number I found: in 2025, creators produced roughly 33 times as much brand-related content as Fortune 100 companies published through their own channels.

Read that last one again. The brands with the biggest budgets in the world are being out-published 33 to 1 by individuals. That gap is your opening.

What this looks like in practice:

• A newsletter to 4,000 operators in your niche
• A ranking position for the search term your buyer types when the problem finally gets bad enough
• A podcast where your future customers come talk to you for an hour, on the record
• A LinkedIn presence where the right 500 people see how you think every week

Now the honest part, because I’m not going to sell you something easy.

None of this is quick. You need the freedom to do it for about two years before it reliably pays you back, and most founders quit somewhere around month seven when the numbers still look like nothing. That 2-year runway is a real constraint, and if you can’t carve it out, be honest with yourself and buy your traffic instead.

But it’s also the single highest-leverage thing available to someone with no local capital. It costs time instead of money, which is exactly the trade you should want to make. And it compounds in a way paid never does. Turn off your ads and the leads stop that afternoon. An audience you built over two years is still there.

Start in month three, not month twenty. The founder who spends year one building product and year two discovering they have no way to reach anyone is the most common failure I see, and it looks like a product problem right up until you check the traffic.

Price like a company that has to make money

Venture-backed competitors price to grow. They can lose money per customer for years because that’s the deal they signed. If you benchmark against their pricing, you inherit their economics without inheriting their balance sheet.

Being away from the hype market helps here. Nobody in your coffee shop is telling you $29 a month is the going rate for something that saves a customer twenty hours. Charge for the value, take fewer and better customers, and let the funded competitor buy the segment that was never going to pay anyway.

Underpricing is the most expensive mistake I watch founders make, and it compounds. You can’t outrun bad unit economics with volume when volume costs money.

Skip the ten thousand person conference

If your city doesn’t have the network, go borrow one. Just not the way most people think.

Everybody pictures the giant conference in Las Vegas. Fifty thousand badges, a keynote in an arena, an expo hall of vendors. I’ve done those. You come home with a tote bag and forty LinkedIn connections who don’t remember meeting you.

The small ones are where the value is:

• CaboPress is the clearest example I’ve been to. Invite-driven, you apply, and there were somewhere around seventy to a hundred people the year I went. Programming ran in the morning and the afternoon, which was the point. The gaps are the event. By the end I’d had real conversations with almost everyone in the room, and the caliber of people was unreasonable for a group that size.
• Vistara does the same for a narrower crowd. A couple hundred agency owners, all wrestling with the same problems, which makes every hallway conversation immediately useful.
• WordCamps are a different flavor. Community-run and contribution-driven rather than curated, but the density of people who actually build things is high and the local ones are cheap.
• MicroConf is on my list for the same reason. It’s explicitly built for founders growing without venture money, which is most of the audience for this post.

The filter I use now is simple. Under 300 people, curated or applied, and the schedule leaves half the day open. That combination is the only reliable way I’ve found to build a real network from outside a major market. Two or three of those a year will do more for you than any amount of local coffee.

Build the org chart your labor market can fill

The lazy pitch is cheap engineers. That’s not what this market is good at, and hiring against a city’s weakness is a slow way to lose.

What’s here in depth:

• Operations and support people, in volume
• Bilingual talent, which matters more than most founders account for
• A steady flow of people leaving the military with clearances and an unusual tolerance for process
• Health system and financial services veterans who understand regulated environments

That’s a spectacular fit for a services-heavy vertical software business with real implementation work. It’s a bad fit for a company whose plan requires ten senior platform engineers by next spring.

Design the company around the labor pool you have rather than the one in the pitch deck template. That one choice decides whether you’re hiring in six weeks or six months.

The part I’d want someone to tell me

None of this is a shortcut. Building this way takes longer, it’s less fun to talk about at a mixer, and you will watch flashier companies in other cities raise money for ideas you think are worse than yours.

What you get in exchange is a company that survives things. When the funding market closes, it doesn’t affect you, because you were never in it. When a competitor’s board changes strategy, you don’t have a board. When someone finally does want to buy you, you’re negotiating from revenue instead of runway.

I’m not leaving. My family is here, my kids are here, and I’m still building here. I just stopped expecting the city to be something it isn’t, and it made me a lot better at the part I actually control.