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

You simply can’t expect to grow a business year after year without growing 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).

So as a bootstrapped Founder you need to be really self-aware about your skills and interests and be intentional about how you spend your time.

SureSwift has scaled quite a bit over 6 years, and I have a team and investors/mentors I can bounce ideas off of, but I don’t have a manager who’s keeping an eye out on my performance or my personal development. So, I make sure to have a check-up conversation with myself pretty regularly (don’t worry, I don’t do it out loud).

✅ 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 in business, I’m fortunate to be at a stage where if I’m not checking all 3 of those boxes (and it’s something that really needs to be done) I’m going to have someone else on the team do it if I have an existing team member who could check them all. Or, I’ll hire someone if it’s big enough and there’s not an existing person who can check the boxes.

When you’re in the early stages of bootstrapping, you’re naturally going to have some roles you fill where you don’t check 3/3 boxes because you’re filling EVERY role in the company. Trust me, I’ve been there.

The funny thing is that I think a lot of 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 doing all of them.

But doing everything was designed very specifically to get the business from zero to one. When you reach ‘one,’ you need to think about changing things. And every Founder is going to define ‘one’ a little differently depending on things like personal expenses, if you have kids and how old they are, if you have a partner who brings in a steady income, your risk tolerance, etc. It’s worth taking a moment to write down what it looks like to you. If you have a Co-Founder, you should both do it, and come to a shared agreement on what it 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.

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

Let me 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 5-year plan can be broken down to a 3-year vision, and that can be broken down to a 1-year plan, and that can be broken down to really specific actions you need to take in ~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.

Start by having 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.

Chunk those into broad business categories like admin, support, product management, development, and marketing. Now assess each of those things against your skills, your passion, and your capacity.

Hire someone part-time to help you with the category where you checked the fewest boxes. This is your first step to scaling and getting past one.

Once you have a great person trained up, put all the time you used to spend on that task/category and put it 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, get after it.

When that’s done, repeat the whole process and check back against your long-term vision/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 that the part of entrepreneurship that they love is the zero to one part.)

Join the Founder’s Squad

Founder stories, advice and case studies.

You have successfully subscribed!