Scaling a Bootstrapped SaaS: How to Not Get Stuck at ‘One’

As a business grows its needs change, and if you’re a founder, that means your role and the skills you need to bring to it change too. The skills you needed last year (or even last month) may not be the ones you need today.

You simply can’t expect to grow a business year after year without improving your skills or hiring out for the ones you don’t have, or building it to the stage you enjoy working on and then selling it.

We know this all too well at SureSwift Capital. Since its 2015 inception, SureSwift has experienced significant growth. The company's Founder and Chairman, Don Wharton, says that assembling a strong leadership team with shared values has been key to this success.

However, if you’re a solo founder, you simply don’t have these mechanisms and resources built in. But that doesn’t mean you can’t grow your business — it just means that you need to be self-aware about your skills and interests and be intentional about how you spend your time.

Keep reading to learn about exploring whether you're ready to scale, checking off the important three boxes, knowing when you've reached "one", and what to do so you can move up from there. We'll also lay out some common SaaS scaling mistakes to watch out for.

Are you ready to scale?

It's crucial that you're completely self-aware about whether your business is actually ready to scale. Sometimes, your biggest challenge can only be resolved by growth. If that's the case, there's a good chance you're ready.

Be sure to assess several factors collectively, including:

• The solutions your customers need and want and how you're delivering or planning to deliver them,
• Whether you've achieved past goals and have a solid place in your market,
• How strong and cohesive your team is, and if they're eager to grow with your business, and
• If you're working with strong cash flows, high recurring sales, and low risk.

Check off the important boxes or find someone who can

Many of us here have a team and investors or mentors to bounce ideas off of, but we don't all have a manager keeping an eye on our performance or personal development. So, it's important to regularly check in with ourselves by asking:

✅ What do I like doing? (passion)
✅ What am I great at? (skill)
✅ What do I have the bandwidth to take on? (capacity)

After several years of experience, if we're not checking all three of those boxes (something that truly needs to be done), we're best off having someone else on the team do it, if possible. If not, we'll hire someone if the task is big enough.

Define what "one" looks like and change things up when you achieve it

When you’re in the early stages of bootstrapping, you’re naturally going to have some roles to fill where you don’t check 3/3 boxes because you’re filling EVERY role in the company. This happens to everyone.

The truth is that many bootstrappers start out recognizing which roles they’re not checking all the boxes on. But along the way, they get used to doing them, and if they see some early business success they get positive mental feedback, so they just keep up this routine.

The thing is, doing everything is designed very specifically to get the business from zero to one. When you reach "one", you need to think about changing things. Now, every founder is going to define "one" a little differently depending on things like personal expenses, if they have kids and how old they are, if they have a partner who brings in a steady income, their risk tolerance, etc.

It’s worth taking a moment to write down what this looks like to you. If you have a co-founder, you should both do it and come to a shared agreement on what "one" looks like. Because as you’re going along, it’s incredibly easy to blow right by that stage and keep doing everything exactly the same.

Take the first step, and then the one after that, and then the one after that

We can’t tell you how many founders we talk to who say, “I want to scale.” They tell us they’re making great MRR, and they’re profitable and growing, and then in the next breath, they say they still personally answer every support email (or do every sales pitch, or code every break-fix… you get the idea).

We'll say it again: That approach got you from zero to one. It will not move you from one to 10 (or to 100, or to 1,000).

So, how do you not get stuck at "one"? It’s really easy to get overwhelmed when you start thinking about scaling and everything you need to do, or every person you need to hire in the next five years to get there.

But that five-year plan can be broken down to a three-year vision, that can further be broken down to a one-year plan, that can even further be broken down to really specific actions you need to take in about 90 days. So, all you really need to do is take the first step, and then the one after that, and then the one after that.

Moving up from "one" — a step-by-step guide

Follow these steps to get your business out of "one" and ready to scale.

1. Have that check-in conversation with yourself. Define what "getting to one" looks like. If you’re already there, define what the next stage looks like and what you need to do to get there.

2. Chunk what makes up these stages into broad business categories like admin, support, product management, development, and marketing. Now assess each of those things against your passion, your skills, and your capacity — just like we defined earlier.

3. Hire someone part-time to help you with the category that received the fewest checkmarks. This is your first step to scaling and getting past "one".

4. Once you have a great person trained up, put all the time you used to spend on that task/category towards the one thing you think will move your business forward the most. Maybe it’s a new feature, maybe it’s refactoring code to accommodate scale, maybe it’s documenting, maybe it’s onboarding, maybe it’s more hiring. Whatever it is, go after it.

5. Repeat the whole process and check back against your long-term vision or plan. Congrats — you’re on your way to scaling.

And if you didn’t check the "passion" box on a good percentage of the "next stage" tasks, take note of that, too. Many of the bootstrapped founders who have sold to SureSwift decided to sell because they recognized what they love about entrepreneurship is the "zero-to-one" part.

Don't make these mistakes when scaling your bootstrapped SaaS

With about 90% of SaaS businesses eventually failing, you can't afford to be one of them when you've barely even started, let alone scaled. This means you'll want to look into some of the most common factors that impede growth in the industry, including too small of a market, a subpar business model, a high churn rate, and product issues.

Be sure not to skimp on doing product research and ensuring your market is ready to receive your offering. Following through in this area will help you maintain high customer satisfaction and a smooth adoption process.

While you're doing everything you can to ensure things go well in scaling your startup, don't ignore some of the common mistakes founders tend to make along the way. Being aware of them can help you anticipate challenges and deal with them in the best and quickest way possible. Some of the most common culprits include:

• Lacking product design
• Suboptimal team (roles and/or size)
• Overlooking market research
• Incomplete or poor planning
• Overcomplicating the product adoption process
• Underestimating churn or solely focusing on acquisition

Scaling a Bootstrapped SaaS FAQs

How do I know if I'm ready to scale my bootstrapped SaaS?

If your biggest challenge can only be resolved by growth and/or you feel good about these factors, you're probably ready:

1. The solutions your customers need and want and how you're delivering or planning to deliver them
2. Whether you've achieved past goals and have a solid place in your market
3. How strong and cohesive your team is, and if they're eager to grow with your business
4. If you're working with strong cash flows, high recurring sales, and low risk

What does "one" mean when scaling a SaaS business?

"One" is the point to which you get your business (from "zero") after a period of essentially doing everything yourself. When you reach "one", you need to think about changing things. Decide what "one" means to you, personally (and agree on it with your co-founder, if you have one), as it's different for everyone. It's too easy to blow right by "one" and keep doing everything yourself.

How do I move up from "one"?

1. Check in with yourself about what "getting to one" looks like. If you’re there, define what the next stage looks like and what you need to do to get there.

2. Group what makes up these stages into broad business categories like admin, support, product management, development, and marketing. Assess each against your passion, skills, and capacity.

3. Hire someone part-time to help you with the category that received the fewest checkmarks.

4. Put all the time you used to spend on that task/category towards the one thing you think will move your business forward the most.

5. Rinse and repeat. Check back against your long-term vision or plan. 

6. Note if you didn’t check the "passion" box on a good percentage of the "next stage" tasks. Many founders sell because the part of entrepreneurship they love is "zero-to-one".

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