Bootstrapping 5 SaaS products with LTDs and a content-first approach with Mike Hill @Curator.io

saas.unbound is a podcast for and about founders who are working on scaling inspiring products that people love, brought to you by https://saas.group/, a serial acquirer of B2B SaaS companies.

In episode #41 of season 5, Anna Nadeina talks with Mike Hill, bootstrapper and serial entrepreneur, co-founder of products like Curator.io, Frill.co, Juuno.co, Flook.co, and Anycamp.

On saas.unbound I get to talk to founders who build products that people love. In this episode I spoke with Mike Hill — serial bootstrapper behind Curator, Frill, Juuno, Fluke and more — about how he builds multiple micro‑SaaS products, why he prefers lifetime deals (LTDs) and content-first growth, and how design and product discipline beat chasing the next shiny idea.

From an ad-agency background to serial bootstrapper

Mike’s route into product was anything but linear. With a background in a digital production agency he sold an ad business, realized he loved building things, and set out to start multiple micro‑startups. The original plan was “10 startups,” but Mike quickly learned the constraint that matters most isn’t money — it’s mental space. He now focuses on fewer, cleaner businesses that he and a small team can actually run and improve over time.

“New ideas are for fools and geniuses. If it’s a new idea, it’s probably a [expletive] idea.” — Mike Hill

Why bootstrapping — and why small

Mike is unapologetically pro‑bootstrap. The advantages he highlighted:

• Control: keep decisions fast, avoid corporate processes that slow adoption of new tech (like AI).
• Resilience: small teams, low burn, and simple economics mean businesses can survive long enough to find product-market fit.
• Lifestyle: the end goal is sustainable businesses that support a life outside the office — Mike values walking his kids to school, fishing, and working on his own terms.

His model: launch small, profitable SaaS products with clear pricing (often low price points) and avoid building huge teams that increase fixed costs and risk.

AI: useful, but overhyped

We talked about AI agents and the hype cycle. Mike uses AI every day and believes it makes engineers and creators more productive — but he’s clear eyed about limitations and the current hype:

• AI is great for certain tasks but not a silver bullet that kills SaaS.
• Firing entire marketing teams and claiming agents can replace them is a short-sighted PR stunt, not a sustainable strategy.
• AI helps bootstrappers adopt capabilities faster than large incumbents, because small teams can iterate quickly.

How Mike picks product opportunities

He’s not chasing brand‑new categories. Instead Mike looks at existing products that have two big problems:

• Poor UX — a great website but a terrible product experience.
• Overpriced — incumbents charging high prices for mediocre value.

So the strategy is: copy the idea that already has buyers, fix the UX, price it more sensibly, and win customers. He shared a real origin story where a competitor’s rudeness motivated the team to build a better, friendlier alternative — out of spite and opportunity.

“Design sells”

Design isn’t just pixels. Mike argues design is craft — animation, interaction details, microcopy and onboarding all matter. He prefers a small, product-focused team where everyone thinks about product and design. That emphasis raises conversions and inspires the team.

Go-to-market recipe for bootstrappers

Mike’s approach to GTM is pragmatic and repeatable. Here’s a condensed version of the checklist he follows for new products:

1. Decide what “good enough” looks like — ship a polished product (the bar for MVPs is much higher today).
2. Run a private LTD (lifetime deal) to raise early revenue and recruit early adopters from relevant Facebook groups and LTD communities.
3. Start charging early — never just give accounts away for free.
4. Write content from day one (not from product launch day).
5. Use AppSumo selectively for reach; ask for reviews and be active on Reddit and Quora.

Mike’s view on LTDs is nuanced:

• LTDs are an alternative to seed funding — they bring money and passionate early users who feel like investors.
• Downsides include long‑term support expectations and occasional account resale problems, so plan LTDS carefully (exclude high COGS features, don’t promise unlimited expensive usage).

Channels that actually work

Mike invests in product first, then content and SEO. He believes paid ads seldom pay for small bootstrapped businesses and prefers evergreen acquisition tactics:

• Write SEO‑first content from day one and invest in backlinks.
• Be active on Reddit — listen to people complain, answer questions, and genuinely help (it’s great for product feedback and LLM training).
• Engage LTD communities and AppSumo for early traction and reviews.

“Write content from the day you start the business — it’s evergreen and pays back for 10–20 years.” — Mike Hill

Team structure and hiring philosophy

Mike prefers very small teams and rigid founder structures. Typical setup:

• Four co‑founders per product (Mike and partner Tom + two others for new businesses).
• Everyone needs to be product-minded — feature prioritization, UX and quality are shared responsibilities.
• Design and engineering heavy: a designer and developers (front-end / back-end split where possible).
• Outsource marketing (content/SEO) if necessary — they accept they’re “bad at advertising.”

He also has a strong rule: “Never work with people you’ve never worked with before.” It’s blunt, but it comes from experience — aligning expectations and tolerating founder quirks is easier with a known collaborator.

Product discipline: fewer features, better core

When a bootstrap SaaS reaches a “sunset” phase (growth slows), Mike prefers to accept a stable business rather than endlessly fatten the product. Key ideas:

• First features move the needle. Later features rarely have the same impact.
• Rather than bloating one product, sometimes it’s smarter to start a clean, adjacent product and chase another ARR curve.
• Focus on usability and clarity — overcomplicating the product risks making the core experience worse.

Real wins and a memorable failure

Mike’s proudest results so far are less about headline metrics and more about lifestyle and product health. He highlighted:

• Businesses that support his life: time with family, freedom, and working with friends.
• A product with an NPS around 85 and ~20% upgrade rate from trials — a promising signal he thinks will be a big win when he nails marketing.

His most instructive failure was Puffling — a job‑sharing matching product. It failed during validation because businesses told him they’d participate (it cost them nothing) but would not commit when the candidates were ready. The lesson: be wary of soft validation and novelty ideas that solve coordination problems in complex ways.

Practical growth hacks and final advice

If you want to borrow Mike’s playbook, here are the most actionable takeaways:

• Start content early. Publish before launch and keep publishing — SEO compounds.
• Use LTDs strategically. Sell value to early adopters, but design the deal to avoid costly long‑term obligations.
• Be product-first. Invest in UX and design — good design converts and makes customers stick.
• Stay lean. Small teams, low burn, and product focus beat big marketing budgets for early micro‑SaaS.
• Use Reddit and Quora. Listen to complaints, help people, and learn what competitors get wrong.
• Don’t chase “new.” Copy proven ideas, but make them noticeably better.

“The aim is for that side hustle to pay you more than your job. But I still don’t want you to quit your job.” — Mike Hill

Closing thoughts

Mike’s approach is refreshingly pragmatic: pick proven demand, obsess over user experience, sell early (often via LTDs), and let evergreen content and product quality drive growth. It’s a model built for longevity and balance — ideal if your priority is sustainable income and independence rather than chasing huge valuations.