Build vs Buy: Bootstrapped SaaS Choices That Win

Bootstrapped founders love building. It feels productive, controllable, and honestly… fun. But “we’ll just build it” is also how you end up with a product that’s late, a marketing plan that never starts, and a monthly tool bill that looks like a small mortgage.

Episode 590 of Startups for the Rest of Us (Rob Walling with Craig Hewitt of Castos) is a goldmine for anyone doing startup marketing without VC. Not because it hands you a viral growth trick—but because it forces the hard decisions most SMB founders in the US have to make: What should we build? What should we buy? When is investor money a trap? And what do you do when the company is alive… but not really going anywhere?

This post is part of the SMB Content Marketing United States series, so I’m framing every lesson through the lens most founders actually live in: limited time, limited cash, and a need for marketing decisions that compound.

Build vs buy: the simplest rule bootstrappers ignore

Answer first: If a tool doesn’t directly improve your customer’s experience inside your product, you should almost always buy it.

Craig’s take is blunt: Castos “almost never” builds internal tools unless it’s core to the product experience. Rob echoes the same idea with the developer reality check: building an “easy” tool isn’t the hard part—maintaining it forever is.

Here’s the build-vs-buy filter I’ve found works best for bootstrapped SaaS and SMB software teams:

The 3-question build/buy filter

1. Does this change customer outcomes?

   • Build when it affects activation, retention, expansion, or trust.
   • Buy when it mostly affects internal convenience.

2. Will this require ongoing product work?

   • If marketing, support, or success will need to edit it, you’re signing up for a “tool product” inside your product (permissions, UI, WYSIWYG editors, QA cycles, bug tickets).

3. Is there a reliable category leader already?

   • Payments, email delivery, analytics, scheduling, bookkeeping—these are solved problems with mature vendors.

A concrete example Rob gives: teams think they can build “simple onboarding flows” instead of paying for tools like Appcues. Then reality hits:

• You now own a UI editor
• Your team needs role-based access
• Every browser update breaks something
• Bugs compete with your core roadmap

If your goal is lead generation and organic growth, every hour spent rebuilding commodity tooling is an hour not spent creating content, running customer interviews, improving activation, or tightening positioning.

What to build (and what to buy) in a bootstrapped SaaS

Build (usually):

• Pricing and checkout flows that shape conversion and trust
• In-app cancellation / downgrade flows (reduces churn and saves support load)
• Core product differentiation (the reason customers choose you)

Buy (nearly always):

• Accounting/bookkeeping
• CRM basics
• Transactional email delivery
• Scheduling
• Customer support/helpdesk
• Product analytics

That last list is exactly where “subscription fatigue” starts. But the alternative is worse: you pay in developer time and distraction.

“Non-technical founder” doesn’t mean “can’t build SaaS”

Answer first: A non-technical founder can build a SaaS business, but doing it without a technical partner is slower, riskier, and more expensive—so your marketing and validation have to be tighter.

Craig is a solo non-technical founder, and his honesty matters: he got lucky with an early developer and says he wouldn’t choose the same path again. Rob adds the uncomfortable statistic reality: non-technical founders are a minority in bootstrapped SaaS.

So what should a non-technical founder do in 2026?

The most practical path: validation before code

If you’re trying to grow without VC, your biggest risk usually isn’t “can we build it?” It’s “will anyone care?”

Before you hire anyone, validate demand in ways that create marketing momentum:

• Run 10–15 customer interviews focused on current behavior (not opinions). The Mom Test-style approach works because people lie politely.
• Pre-sell: a paid waitlist, a deposit, or a pilot agreement beats “likes” every time.
• Start content early: publish 6–10 pieces aimed at the niche you’re targeting. If you can’t attract attention pre-product, the post-launch version will be harder.

Here’s the stance I’ll take: If you can’t describe your first 100 leads, you’re not ready to hire a developer. You’re ready to do marketing.

Where to find developers (without gambling your runway)

The episode names the usual suspects (Upwork, Toptal, agencies), but the deeper point is this: the “finding” part is easy; the risk management is the hard part.

To reduce downside:

• Hire for a 2–3 week paid prototype with a very tight scope.
• Use a staged contract: prototype → MVP → hardening.
• Require weekly demos (if they can’t show progress, you have a visibility problem).

And if you’re looking for a technical co-founder, treat it like a long process. Rob’s analogy holds: it’s like dating, except if it goes wrong you also inherit a messy codebase.

Competing in crowded markets: positioning beats features

Answer first: In a competitive space, you win with a sharp position and a reliable acquisition channel—not by matching your competitors feature-for-feature.

This is where the episode fits perfectly into the SMB content marketing theme. Small teams can’t out-build incumbents. But they can out-position them.

Craig’s Castos example is a classic bootstrapped move:

• Pick something you can own (early on it was WordPress integration)
• Then double down on a category wedge (private podcasting workflows)

The 4 ways bootstrapped companies win crowded categories

Rob mentions a framework that’s still useful:

1. Unique positioning (be opinionated)
2. An audience (people already trust you)
3. A network (partnerships, ecosystems)
4. A distinct traffic channel (SEO dominance, marketplace listings, integrations)

For SMB founders in the US relying on content marketing, the two most repeatable are:

• Unique positioning: “We’re for X, not everyone.”
• A distinct traffic channel: usually SEO, YouTube, LinkedIn, or an ecosystem like Shopify/WordPress.

A practical positioning checklist (you can use this week)

If you’re building “a community platform” or “a social media tool,” your copy will default to generic unless you force specificity.

Answer these in one page:

• Who is it for? (“Ops teams at 10–50 person HVAC companies” beats “SMBs.”)
• What painful job does it replace? (“Stops lost leads from Facebook DMs” beats “improves engagement.”)
• What do you refuse to do? (“No enterprise workflows, no seat-based pricing.”)
• Why now? (New regulation, channel shift, buyer behavior change.)

If you do this, your content marketing gets easier because each post has a point of view.

Zombie companies: why “some revenue” can still be a trap

Answer first: A zombie company is one that’s operationally alive but structurally stuck—especially when investor expectations and founder goals no longer match.

One listener question in the episode is the nightmare version: raised two small rounds, valuation got weird, company pivoted, now it’s break-even but not a venture-return trajectory. Friends and family want money back.

Craig says something founders need to hear before taking capital:

When you take investors, it’s not just your business anymore.

And I’ll go further: friends-and-family money is often the most expensive money you’ll ever take, because the emotional cost can be brutal.

What to do if investors want liquidity but the business isn’t ready

Rob and Craig both lean toward: don’t panic-sell just to partially repay investors—especially if it wipes out founder upside.

Your options typically look like this:

1. Reset expectations in writing

   • Share the reality: selling now returns ~0.75x, waiting may return more.

2. Offer a structured repayment plan (only if cash flow supports it)

   • This can be a small quarterly distribution or revenue-based payback.

3. Pursue growth with a clear timeline

   • Lifestyle pace + investor money don’t mix well. If you want lifestyle, don’t take investor money next time.

If you’re pre-funding right now, the prevention is simple: if an investor can’t emotionally afford to lose the money, don’t take it.

The “boring” ops stack that protects your marketing momentum

Answer first: Clean books and simple ops tooling reduce founder stress—and stress is what kills consistent content marketing.

It’s a small section of the episode, but it matters. Craig recommends Bench (software + service). Rob mentions Xero paired with a bookkeeper.

Why include this in an SMB content marketing series? Because founders underestimate how often marketing stalls due to operational drag:

• You avoid running ads because tracking is messy
• You don’t know CAC because bookkeeping is behind
• You stop publishing because you’re dealing with taxes and cleanup

A steady marketing engine requires boring infrastructure.

Founder communities: the cheapest form of accountability

Answer first: A mastermind is a force multiplier for bootstrapped founders because it improves decisions, consistency, and resilience.

Rob shares that MicroConf mastermind matching has produced 600+ matches across 50+ countries and 20 time zones, with a collective ARR north of $150M (as stated in the episode). The numbers aren’t the point—the mechanism is.

If you’re building without VC, you need something that replaces the external pressure of investors. A good mastermind does that without taking equity.

Here’s what I’ve seen work:

• 4–6 founders
• Similar stage (within ~2–3x revenue range)
• Weekly or biweekly calls
• One measurable commitment per meeting

It’s not “motivation.” It’s structure.

What to do next (if you’re trying to grow without VC)

The episode’s themes all point to one operating principle: protect your focus. Build what differentiates, buy what commoditizes, and make marketing a first-class activity—not an afterthought once the product is “done.”

If you’re a bootstrapped founder in the US relying on SMB content marketing, pick one move for the next 14 days:

1. Write a one-page positioning doc and update your homepage headline.
2. Cut one internal build project and replace it with a paid tool.
3. Run five customer interviews focused on current behavior and spending.
4. Publish two pieces of niche content aimed at a single buyer role.

The big question to sit with: what are you building that your customers will never pay you for—and what would happen to your growth if you stopped?