Bootstrapped Founder #82: Accountability Systems for Founders

Dear founder,

If you prefer listening over reading, you can listen to this episode of The Bootstrapped Founder on my podcast.

Some days, I don't feel like doing anything entrepreneurial at all. It's not that I'm burned out or disinterested, not at all. But there are those days where all I want to do is curl up on the couch and read a good book.

Often, I take the day off and indulge in whatever distraction I crave. It's fun, it's filling up my creativity well, and I get back to my work the next day feeling refreshed. But sometimes, the lull lasts for longer, and it starts threatening my overall output.

It's easy to take a break from producing things. The hard part is to get back to doing it.

Very early in my entrepreneurial journey, I learned that I needed checks and balances in place if I wanted to build something successful. My motivation isn't a constant stream: some days, I am hyper-motivated to write and build; others, I can't seem to put a word to paper or write a single line of code.

With these fluctuations of my intrinsic motivation, I learned that I needed external stimulation. Something that would remind me of the larger purpose of my work.

I needed an accountability system.

And I am not alone. Many founders, no matter if they are solopreneurs or part of a team, need to build a structure that allows them to compensate for whatever reasons to procrastinate their minds come up with.

Since we all have unique challenges, we have found a multitude of accountability approaches. Some involve other individuals, groups, or whole communities.

Building In Public

As entrepreneurs, we have the incredible luxury of being able to tap into a global community of like-minded founders. Great advice is just one Direct Message away. We are part of a knowledge graph of incredible proportions.

Some founders have started using that to their advantage. They share their progress with their community at large. On Twitter, that entails publicly sharing thoughts, choices, and milestones on their path to building a successful business. Every consideration, every newly built feature, every quirky customer service conversation is a new tweet, an opportunity to engage with the founder community.

Founders who communicate their progress like this share their journey as it happens. They share the good and the bad. Successes and struggles alike find their way into the public discourse, inviting commentary, empathetic support, and making the founder and their business more human and visible.

It is in moments of uncertainty and hardship that building in public really shines. Instead of being limited to a subjectively limited perspective, these entrepreneurs publicly ask the questions that other founders would only ask themselves. The results of these conversations tend to be incredibly eye-opening. More often than not, experienced founders jump into the conversation and share hard-earned insights within minutes after a question is asked.

Building in public is crowd-sourcing decision-making. It's getting expert opinions at scale.

Now that's mostly connected to input — what about accountability?

It turns out that sharing your progress in public creates a loyal follower base of people who want to see you succeed. I am building a SaaS in public, and I write my books in public as well. Consequently, people reach out to me regularly, asking about my progress or if they can help. When I don't talk about a particular project for a while, people who remember that I committed to something a while ago will resurface that project to me and encourage me to keep going.

Building in public is commitment-in-public. Once you start sharing progress, people expect more to come. For that to happen, you need to continue working on your projects.

Mentorship

Tapping into the knowledge of the crowd is a great way to get additional perspectives, but it can be quickly overwhelming. If you have thousands of people share their opinions, you'll see conflicting advice, and it's hard to know which is more applicable to your business.

There are people out there who can help you contextualize advice and apply it to your business. Those people are called mentors: successful and experienced founders who have been there before and understand the subtleties and uniqueness of each entrepreneurial journey.

Finding a mentor to guide you along your path isn't as easy as sharing your progress in public. Mentorship is an active two-sided relationship, and if you want to be a mentee, you have to get a mentor to commit.

Now, there are varying degrees of mentorship, differing primarily by how often you communicate and how in-depth your mentor's knowledge of the business is. Mentors are sought-after experts who usually are pretty busy themselves. They won't be able to spend many hours a week helping you with your business.

A permissionless apprenticeship is an approach that short-circuits the need for your mentor to agree to a relationship. You just start working for them, asking for nothing in return, but opening a line of communication. More often than not, this enthusiasm will lead to an actual relationship with that person — which can turn into a long-term mentorship. It usually starts with a DM or a conversation in the replies of a tweet.

Mentorship platforms such as MentorCruise allow you to find mentors who will regularly stay touch with you for a monthly fee. It's a mix of consulting and long-term mentoring, and I've been a mentor on this platform with great success in the past.

You can also find mentors by joining accelerators or getting funded by the likes of TinySeed or Earnest Capital. Both are bootstrapper-aligned funding options that come with impressive mentor networks.

Mentors will keep you focused on the things that matter for your business. When I see one of my mentees working on pointless but easy-to-build features instead of talking to their customers, I will call it out. My job as a mentor is to keep them accountable. Their job is to want to be accountable to me.

Paying for mentorship is fine. I might be biased here, but I believe that value should always be compensated.

Accountability Groups & Masterminds

If you don't want to report to a single person, you might find a better solution in practice-driven accountability groups. A great example is the Weekend Club, a support network for founders working on a side project. People show up on weekends — and they expect you to show up too. Communities like this are motivation generators. They thrive on the momentum of the combined activity of all their members. The more active you are, the more you'll encourage others to keep you motivated.

Another more intense version of these groups is Masterminds. Usually being invite-only, these small groups consist of founders who are roughly on the same level of experience. The purpose of these groups is to confidentially discuss high-importance topics and support each other during the day-to-day affairs of running a business.

No matter what kind of group you find, you will build long-term relationships with the people you meet there. I've made life-long friendships from experiences like this.

(Fake) Investor Updates

If you're a bootstrapped founder, it's likely that you don't have any institutional investors to report to. That's great in one way, as it allows you to keep all the value you create with the business. On the other hand, it also keeps you from having a well-oiled accountability system. Any VC-backed founder is used to keeping their investors in the loop regularly. Sending out investor updates becomes a common founder activity and establishes immediate feedback loops with other stakeholders.

So, how do you do that as a bootstrapper? You send out fake investor updates: in the style of permissionless apprenticeship, you write an update email once every month, and you ask the people you admire and seek advice from if you can send it to them. Some will say no, but most founders will be curious and — most of all — willing to help you be accountable.

Any entrepreneur will do. Founders on your level, more successful ones, or even those who just started out: sharing your thoughts and plans with a diverse group of people will result in a diverse range of replies.

There are plenty of resources on how to write a solid investor update, so find a structure that works for you. As an added benefit beyond the feedback you'll get from your fake investors, these updates also serve as a historical snapshot of your thoughts and activities in your business.

The more elaborate you are in sharing your reasoning, the easier it will be for people to point out obvious flaws or share relatable anecdotes from their own experience. Since you won't write such an update every week, you can be as verbose as you like. Brevity is great in Tweets, but when it comes to the choices you make for your business, a little more context goes a long way.

The wonderful thing about these fake investor updates is that they will establish a relationship that might turn into exciting opportunities down the road. Customers, partnerships, and even acquisitions are all likely outcomes of regularly showing up and demonstrating how trustworthy you are.

If you commit to sending out an update every month, you need to have done something every month.

Working with Expectations

It's that looming feeling of someone expecting you to have done something regularly that is the core of an accountability system. When I started writing regularly after selling my SaaS FeedbackPanda, I knew that I needed to put such an external method into place.

I started a weekly newsletter. I knew that if there were even just one person who'd subscribe to the newsletter, I'd feel obligated to provide them with something every week.

As I am writing this, I am aware that several thousand people are subscribed to my newsletter. Whenever I feel like I can defer writing to the next day, I consider that a few of those people would be really disappointed if I missed a week of sharing my thoughts. That's enough to get me to start working on my content immediately.

Habits and Pacts

Whatever path you choose for external accountability, there is always a way to be accountable to yourself. In his book Indistractable, Nir Eyal suggests making pacts with yourself to build effective habits. The general idea — do read the book, it's very instructive — is to set up rules that, if broken, cause some minor yet noticeable loss, like having to put a dollar into the swear jar after cursing. Translated into our entrepreneurial world, consider tiny self-punishments such as delaying gratification or limiting the time spent on entertainment.

But don't overdo it with the punishments. Accountability should be a good thing. Maybe consider setting up little rewards for reaching mini-milestones. Just posted your 10th content tweet of the week? Grab a beer. Wrote another 300 words on that blog post for your company blog? Cat video YouTube for half an hour. The bigger the effort, the bigger the reward should be.

Whatever system you end up setting up for yourself, remember that it's there to serve you, not the other way around. Entrepreneurial systems are extensions of the founders, not opportunities for them to be busy. Ask around in your community, observe how other founders keep themselves accountable and try out a few methods. We all have our unique ways of keeping focused, and it might take a few tries to find a compatible method.

The goal is to find a way that aligns your motivation with your mission. At that point, accountability will be a natural consequence of your actions.

Thank you for reading this week's edition of The Bootstrapped Founder. If you like what I wrote about, please forward the newsletter to anyone you think would enjoy it too.

You can find my book Zero to Sold at zerotosoldbook.com. It is being sold on Amazon, Audible, and Gumroad.

If you want to help me share my thoughts and ideas with the world, please share this episode of the newsletter on Twitter or wherever you like, or reach out on Twitter at @arvidkahl.

See you next week!

Warm Regards from Berlin,

Arvid