I Bootstrapped 5 SaaS Products With This One Strategy

Anna Dan: Hey there, welcome to SaaS Group Podcast, I'm your host Anna Dan, head of growth at SaaS Group, so we acquire and buy wonderful SaaS businesses to take them to the next level. And here I chat with SaaS founders and experts to get insights into how they make their business a success.

So today with me is Mike Hill and he's making a lot of businesses a success. So there is Juno, Curator, Flook, Frill, I might be missing a few.

Mike Hill: You're missing two, but one of them is about to launch in two months time, but you've got most of them.

Anna: Okay, all right, well, welcome to the show.

Mike: Thank you, thank you. Great to have you here.

Anna: I think I've been following like one or another for some time and it's always been interesting, like following you on Reddit because you're very transparent there. But you know, how did you get to do what you're doing in the first place?

Mike: Okay, so about 20 years ago I was one of the world's worst developers, I was a Flash developer. It's my first job out of university. I did a degree in zoology of all things and somehow ended up being a developer and ended up in a digital production agency.

And at the end of a very long night with some friends who owned the agency called Holler, I just sort of blurted out, look, I've met a girl. I'm going to Australia. What do you think about Holler Australia? I'll go and set it up for you and they were like, okay, let's do it.

Before I knew it, I was coming out here and I set up a production agency which turned into an ad agency which I sold a number of years ago. I realized over a number of years that I didn't really like advertising and I didn't really like where my career was going. I just loved building stuff.

But I wasn't a very good developer, but I understood the development process. And so when I sold Holler, I had this idea to build 10 micro startups. I thought, well, as an agency person, you can manage 10 clients and you can manage well over 10 projects. And that was stupid. I definitely can't do 10. But we've managed to do five.

I just got back to building stuff, working with people that I worked with in a previous life. I've literally got a rockstar list of all the people I've worked with in my life. And I called them up every now and again and say, hey, do you want to do something together? And sometimes they say no. Sometimes they say yes. And when they say yes, we go out to market, look for something interesting to do and start building it.

I think seven or eight years ago, we started our first SaaS business, myself and Tom. And I never really thought it could get as big as it was going to get. But it just kept growing, kept growing, kept growing. And paradoxically, the more it was growing, the less work we were doing on it. Because we had built all the features — not all the features, I'm being facetious — but the more we grew, the fewer features there were to build.

And so we sat around and we were like, well, can we do this again? Take the same model that we did on Curator and apply it to something else. And so we did it and then we did it again and again and again.

I said the idea was to create 10, but I just can't keep 10 businesses in my head. It's not about the actual work — it's about the mental space of being able to keep 10 businesses in your head. You might as well be an investor, not a founder.

So we've got five different businesses, all bootstrapped. Love bootstrapping. I don't think I know anything else. And I'm a terrible employee, a nightmare employee. So that's where it starts. Bootstrapping kind of suits me a little bit better.

Anna: So I mean, there are AI agents now. Maybe you can outsource five more businesses to them. But we'll get there because the reason this episode is happening is because I saw you comment on one of the LinkedIn posts about AI agents and you were like, no, nobody's really doing it. And I was like, yes, okay, thank you. Honestly, I haven't figured the agents out. They're a mess every time I try to set something up. I was like, yes, that's the person I want to talk to.

Mike: Yeah, look, the agents — I mean, God, I'm probably not the right person to talk to about agents or even AI because I — I preface this with I love AI. I use it in my life for almost everything. What I don't like is people saying things that it can do that it can't do. And this hype is insane.

I think we're in a bubble right now. I'm not sure if it's a financial bubble, but definitely a hype bubble. I think we're starting to realize that AI is great at certain things.

I keep seeing posts about how SaaS is dead. And whenever I ask people — look, just give me one example. Is there one vibe-coded app out there that's making money? I have found a few, but I have asked everywhere. And it's just crickets. Nobody comes up with answers. It's, oh, yes, nearly there. Nearly is not even halfway, right?

This idea that SaaS is dead because of AI — I think SaaS is going to get better because of AI. I think that the day of the bootstrapper is now because it's going to affect the big SaaS businesses that are $10,000 a month. That's a problem, I think. If I was one of those businesses, I'd see AI as a threat.

The bootstrappers like myself — it's just something that makes us better. We can adopt it faster from a coding point of view. It makes engineers better. The big corporations can't adopt AI. They've got processes in place. They just can't, they don't know how to use it properly.

What I really do hate is those posts where people say, I just fired my entire marketing department and replaced it with an agent. What a waste of lungs and blood that person is. Why would you go on LinkedIn boasting about that? That's not how I'd like to do my business. Use AI to actually grow the business, not cut costs. Anyone who's looking to cut costs is the wrong way of thinking.

Anna: Totally agree. So there is something that you said on Reddit. You said you're not building anything new — you're going after something that's already there, usually where the UX sucks, and rebuilding it. And you think design sells. But still, there are a lot of very bad websites out there. So there are plenty to choose from. How do you choose?

Mike: Okay, I'll tell you two stories. One I've never told before.

The second business that we picked was purely because we were looking for a business to build. We knew we wanted it to be a B2B SaaS business. And we got a call from one of our clients on the first business saying they wanted to integrate with Business A. So we went to speak to Business A. Business A was so rude to us for no reason whatsoever. And I just got really angry and said to Tom, I hate these guys. Let's just build their business.

And so that's what we've done. We're now competing against them. And it was purely out of spite. And now we've got a better product than them. It's cheaper.

But that's not a strategy. What we normally do — when we're looking for a business to build, we just looked around the market. Usually with the first business, we needed a bunch of other SaaS tools. We needed a feedback tool, an onboarding tool, an analytics tool. When we went out to market — oh geez, that one's really expensive. Why is that so expensive? It's just data transfer. That one looks good on the surface, but wow, the usability is awful. Great website, awful product.

A combination between bad UX and being overly priced. SaaS had this golden age where you could just charge $1,000 a month. Bootstrappers are now coming in and saying, actually, that could be a $49 a month SaaS business.

I spent my entire career in advertising trying to come up with new ideas. After I sold my ad agency, I had to unwire my brain because new ideas are for fools and geniuses. Especially in SaaS — if it's a new idea, it's probably a shit idea, let's be honest. New ideas are too risky. I don't want to create new ideas. So we're just looking at existing ideas done badly.

I think it's a lot harder to do these days though. Five years ago, ten years ago, it was a lot easier. Everyone had the same idea. It's hard to find a business worth going after now.

Anna: And the way — I mean, if the solution already exists, obviously there are buyers. So how do you acquire customers? I have a quote from you on Reddit where you talk about go-to-market. You say: decide what is a good enough MVP, offer an LTD, go find LTD Facebook groups, never give an account away for free, start charging early, write content, launch on AppSumo, ask for reviews, and always answer questions on Reddit and Quora. Are you taking the same approach with Smile?

Mike: Exactly the same approach. We haven't found a better way. We haven't found a better way when you've not got a lot of money.

Our approach has always been build the best product you can. Not an MVP — build the best product you can. MVP is — I still hear people quoting the Lean Startup and thinking it's some sort of gospel. It's irrelevant today. You launch an MVP by that book's standards today, people won't use it. The bar has changed. You launch the best product you possibly can. Which I suppose is the MVP, but the MVP bar has just changed.

We always do an LTD, a lifetime deal. Some people swear blind it's the wrong thing to do. We've found it really good. Launch a private LTD — go and speak to people in Facebook groups. Launch a plan that rewards your early adopters. Try and make an amount of money — could be 10 grand, 20 grand, 100 grand.

It's just an alternative way to raise seed capital without giving away equity. Is it perfect? No. All these LTD deals are a debt on your ledger — they need to be fulfilled. But if you go through Y Combinator these days, you'd be lucky to get out of there owning 51% of your own business. So six of one, half dozen of the other — I'd rather fund it through payments.

And you're not just getting the money. You're getting users. People who use your product, give you feedback. The LTD community is amazing. It's a very cutthroat community, but they will be your greatest advocates. They see themselves as investors in your business. If you treat them right, they'll put you on a pedestal and get you that initial velocity to MRR.

Sometimes we go on AppSumo. The reach those guys have is insane. Then once the LTD is done, we shut it down. Never to be done again. And then you hold your breath.

Anna: I thought it was a very demanding group. Founders I've talked to who've done LTDs say 13 years later, people who bought for nine bucks are still there saying, why am I not getting this new feature?

Mike: Yeah, we just deal with it. That was the deal. You sold them a lifetime deal and that's the deal. You can't then ten years later go, sorry, I didn't mean that.

But to be perfectly honest, if you sell 100 LTDs, in ten years' time, only one of them is going to be in use. The other 99 will be lost to dead email addresses and people forgot they even bought it. I don't think it's a real problem.

There is a slight problem with people reselling accounts. Someone buys an LTD for $59, waits five years, and sells it for $500. And then you've got to onboard that new person.

But a lot of founders have got to remember that community got you out of the trenches. They'll give feedback, they'll give reviews on TrustPilot. So it's a give and take relationship. As we get older with each business, we get less support requests from LTD customers. So it's really not a problem.

Having said that, I wouldn't start an AI business or anything with massive cost of goods with an LTD. Absolutely not. I heard about a video platform on a lifetime deal — unlimited — it's just crucifying for the business.

Anna: So I want to talk about growth and how you acquire customers. You talk a lot about SEO. Reddit and Quora are also part of your playbook. How do you do it? Are you writing it yourself? Do you have a team?

Mike: I do pretty much all of that myself. Anything on Reddit, anything on LinkedIn, I do all of that myself.

Every business is structured differently. It's me and Tom as the core co-founders and then with any new business we partner with two other co-founders. So any business has four co-founders.

One of the things I absolutely stress to everybody is that this is your side hustle. This is not your main job. 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.

This idea that velocity and speed in startups is important — it can be, but it's not the most important thing. Staying alive is the most important thing. All of my businesses, we could take it right down to the wire, minimum costs and just stay alive. We never have to close it down. It's a war of attrition. The only thing that will stop us with this strategy is getting bored and giving up.

We try and keep the team minimal. We hate hiring people. More people, more problems. That's the fastest way to burn cash. These businesses are not meant for exits. The exit is the cherry on top. The idea is ludicrous salaries and then an exit at the end.

We invest in tech. We don't invest in marketing. The irony is that all of us used to work in ad agencies and we're all terrible at advertising. But we invest in product. It means slow growth, very linear, but as long as you stay alive and don't get bored and don't give up your day job, you can't be beat.

Your competitors running at $500 a month are going to run out of steam a lot quicker than you will.

Anna: I feel like SEO and being active in social media is marketing enough for a good product. And as a marketer, I truly believe that no amount of marketing is going to save a shitty product. Not long-term.

Mike: Every product should be a PLG product. It doesn't mean there are no salespeople or marketers. It just means you value your product and try to make the best out of it.

Anna: You said at the beginning that as the product grows, there are fewer features to build. I loved that. Because honestly, looking at all the founders and companies I've had on the podcast, I feel like at some point it's just growth for the sake of growth. Let's add more features. Nobody is asking for it. Sometimes it's not necessary and it just complicates the product and confuses the customer.

Mike: You actually run the risk of making the core product worse.

Every bootstrap SaaS business, unless you have positive net revenue retention, is going to reach a sunset point. Growth starts to slow down. You've got to make a decision — do we build more features, make the product fatter? Or do we go, actually, it's easier to build a new adjacent product and get that $1 to $2 million ARR again.

Most SaaS businesses won't plummet once they hit their sunset period. Let's call it $2 million ARR — they're not going to drop to $1 million. They stay around $2 million because input matches output. So you've got to decide — put 100 extra hours a week to get to $2.1 million, or put all that effort into starting something new.

That's when we decided people don't need more features. There was nothing left to build. The first 50 features had all the impact. Accept sunset mode. Build something else.

I'm not sure I'd do that again because there are so many products for everything these days. Customers look at a hundred options and just pick one — they're not going to spend loads of time analyzing for $50 a month. So we lose a lot of customers to crappy products. Not because they're better, just because the feature list looked right.

It's harder today. When we were starting out, we were finding 10-20 ideas a month. I haven't got excited about a new idea in the last year.

With Flook, one of the things we do is wage a price war. It does two things: gets us new customers who can't afford the incumbent, and stops people like me from entering the industry. It's too much work for $50 a month. So it protects you on both sides.

Anna: So what happened with Smile? It's been there since 2021.

Mike: Yeah. We just had the wrong team. We couldn't get the team jelling. We went through three teams and it just didn't work. We put it aside for a year.

Finding the team is so tough. I have this rule — lightly held — never work with people you've never worked with before. That's not because I don't know who they are, it's because I'm a nightmare. I change my mind all the time. If you've worked with me before and decide to work with me again, brilliant — we know we're not going to have problems.

Picking the team is the biggest reason why any project fails. I love working with all of my co-founders. They're all friends outside of work. We all have a laugh. I never have that work dread — that Monday morning “fuck it” feeling. I'm pestering them on the weekends. “What about this feature?” “Shut up, Mike. It's the weekend.”

You've got to be comfortable with your team. Getting four people to work together, pulling in the right direction, knowing they won't be paid for a year or two — it's tough. But you get the right people who just love making shit, it works.

Anna: So what's the perfect team? Developer, marketer?

Mike: I still think of myself as a product person. My brain energy is all spent thinking about features. I think everybody in the company needs to be a product person.

We don't have any marketing people. We outsource marketing because we're all shit at it. When I say marketing, I mean writing and SEO. We don't do any outbound. Tried it, failed miserably. Paid media is a waste of money for small businesses — probably because I'm doing it badly. We spend a little bit on Google as an offering to the Google Gods. Make sure they don't turn off our SEO.

The ideal team is design and development. Heavy on tech. We separate backend and frontend. And I always like to have a designer on the team. I strongly believe good design sells.

All these people saying “I'm skipping Figma because I just develop straight in Cursor or Bolt” — yeah, it shows. Have you seen your product? It looks like crap. It looks like every other product out there. Design is a craft.

We argue over every pixel. But I think it shows in the work. And I love it. I don't want to work on a crappy looking product. I take pride in that.

Good design is not just pixels. It's animation. When you click a button — does it animate? Does it feel squishy? Does it feel quick? All of those things are super important.

Look at Instagram. There were a hundred businesses doing what they did. There was Hipstamatic. But Instagram's design was so much better. They believed in the craft of how people interact with their product.

I know a lot of successful businesses with crappy websites who've managed to describe what their product does and the problem it solves really well. It's just important to me. You don't go out walking around town in a clown outfit. You like to wear nice clothes.

Anna: Last couple of questions. Five businesses, 20 years of SaaS — what's been the biggest win and biggest failure?

Mike: I haven't had my biggest win yet. That's coming. One of our businesses is skyrocketing. Our NPS is 85 for a SaaS business — that's insane. 20% of people who sign up for a free trial upgrade. But nobody knows about us. If I could work out how to be a good marketer, that business is going to be my biggest win.

Or maybe Smile. Smile has this one thing I didn't realize was so important — total addressable market. If you pick something with a massive TAM, you can fuck up and pick up one percent and still succeed as a bootstrapper. The bigger the addressable market, the more chance you have. With Smile, I walk down the street and go — you could be a customer, you could be a customer, you could be a customer. Anybody with a job could be a customer.

But honestly, my biggest win is being able to walk my kids to school whenever I want. Being able to go spearfishing and fishing any day I want. Having SaaS businesses that support my lifestyle rather than having the business run my life. I couldn't be happier where I am right now.

Biggest failure: I started a business called Puffling, which aimed to solve gender diversity at a senior level. It was a dating app that targeted back-to-work moms who only wanted two or three days. We'd pair them together as a full-time equivalent and sell them into businesses.

In validation, we'd go to businesses and say, would you like to trial this? Nobody's going to say no to a gender diversity initiative. They all said yes. And it was fake validation. When we tried to actually place people — “sorry Mike, I don't think the business is ready for a job-sharing pair.” Why did you say yes? They said yes because it cost them nothing.

And it was a new idea. Don't come up with new ideas.

Anna: The last question is always about hacks. Anything that works for you that other founders would appreciate?

Mike: Two things. Writing content. Write content from the day you start the business — not from the day you have a product. It's not a hack, everyone knows about it, everyone puts it off. Just start writing content. Do backlinking if you can. Pay someone to do it. It's evergreen. It'll pay you back for 10, 20 years.

Don't spend money on ads. God, Google's system is the most dishonest ad system I've ever come across. You say “exact phrase — painter” and they'll go buy ads for “how's the color red?” They're designed to waste your money. Spend money on content instead.

Get onto Reddit. Listen to people moan. Listen to people who are upset about your competitors and interject. “Hey, how about you try this. Full disclosure, I'm a co-founder.” It's been really good for us. And Reddit influences the LLMs — the more data you have on Reddit, the more you're going to influence the LLMs.

Content and just get out there and speak to people. It won't scale, but it'll keep your team fired up. Whenever that Stripe bell rings — it's brilliant, especially in the early days. You know you've succeeded when you turn off the Stripe bell because it's annoying you.

Anna: Super cool talking to you today. Thanks for being very transparent about the experience.

Mike: Yeah, it's been fun. Thanks for your time. Take care.