The Bootstrapped Founder Newsletter Episode 39 – August 7th, 2020

Dear founder,

If you’re coming from a professional background in salaried positions, the chances are that you’ve never hired anyone before. And even if you have, hiring someone for your own business will be a daunting task.

It certainly was for me. I thought that I could manage all that work by myself just fine, so why bother hiring. But I limited myself by doing things that kept me from doing more meaningful work. I was spreading myself too thin, trying to multitask when each task would have deserved my full attention.

Sure, it’s great to help customers through live chat. But should I not have spent the time fixing the very issues they complained about? Could someone else not have a friendly conversation and show them a link to the article in the knowledge base where all the steps were laid out? Most importantly, did it really need to be me?

The Mistakes I Made When I Thought I Didn’t Need to Hire

My first mistake was to think that it would only be reasonable to hire when there would be enough work for a full-time position. To this day, I don’t know why I didn’t think of hiring someone part-time, but to me, a job was a full-time endeavor. This resulted in a strange scenario: I never felt it would be enough work for a hire, because not only could I do it myself, but I would also fit other things into my workday. The fact that I worked 12 hours or more every day of the week seemed to not have registered in my entrepreneurial brain.

Hiring someone could have saved me countless hours of work every day, freeing my mind from focusing on the mundane parts of the business at all times. Sometimes, in between customer service chats, I would get a glimpse of what that life could be. I just shrugged it off, but I should have acted on that initial feeling and hired someone to help me.

My second mistake was to think that onboarding a new hire would be too much work. It turned out that waiting to onboard a new hire is even more work, as it just adds all the tasks you don’t get to delegate on top of the onboarding efforts. I completely misjudged how effective other people can be at learning a new task. I also underestimated the impact of being well-prepared by having built a sellable business.

If you’re using Standard Operating Procedures in your business, the effort of onboarding will be rather low, as you can just give the new employee access to the relevant processes and documentation. Provided that you created meaningful, exhaustive, and instructive documentation, your new hire can explore the scope of their job and prepare for what is to come.

How and Whom to Hire

You always hear that you should hire slowly. That’s true; you don’t want to waste resources when you could do it yourself or build automation to take care of it. But once you see that you’re stuck doing work you don’t enjoy that others could do for you, hire quickly.

Choosing what position to hire for will be a very subjective decision. After all, your preferences and tolerance for doing certain jobs are uniquely yours. Only you know when enough is enough.

In most SaaS businesses, customer service positions will be the first ones for which you may want to hire. While software can scale indefinitely, you can’t. Once your customer base grows, you can automate as much as possible, but there will still be unforeseen problems at random points in time. Finding someone to triage these issues and sending only the most important ones through to you will free up significant space on your calendar and in your mind.

Marketing and sales positions can also be hired for quite early. For all three roles, you, as a founder, must instill the voice and tone of the messaging into your early employees. Until now, you have always been yourself, speaking to the customers the way you speak. It’s essential to keep this style consistent.

Hire someone for the work that annoys you most. Repeat until you enjoy all the work you do.

How to Find Your Perfect Hire

There are two places that I recommend checking out before you head over to the regular job portals and recruiting agencies: expert communities and within your customer base. I’ve found both to yield excellent results in multiple startups I’ve been with.

Expert communities work extremely well for finding developers, designers, and marketers. As a bootstrapped founder, you are at least partially a developer, designer, and marketer. During your entrepreneurial journey, you will have encountered the communities where other professionals hang out. You will likely even have asked a few questions or chatted with other founders. When you are looking into hiring someone, go into the communities that you found most inviting, and offer the job there first. You’ll pre-filter your applicants that way, and have a much higher chance of finding someone who will fit your culture.

Your customers can be a hunting ground for potential employees as well. Particularly for marketing and customer service positions, there are a lot of opportunities when searching for candidates among your customers. No one knows more about the struggles and needs of your customers than your customers themselves. That makes them ideal candidates to take over the jobs that involve talking to prospective or existing patrons of your business. They speak their language, and they know their pain even more than you. They are destined to build bridges and foster relationships with people they innately understand.

I had great success with both kinds of communities both within FeedbackPanda and at a previous startup. Hiring customer service experts from within our customer base was particularly effective in both cases. If you find a person who is looking for something new and is already aware of your company, all it takes is for them to have a background in the field. As people change jobs every few years, it’s not uncommon to find a marketing expert who has become a teacher or a customer service professional who also is interested in local food logistics. You don’t know what talent slumbers among your customers until you ask.

It will always be hard to convince people to join a small business. You’ll need to have a good pitch ready, as you will need to convey your vision of the business and the part that your new employee will play. You’ll need to make clear how they can grow professionally in their new position. This may be a hard thing to verbalize, particularly when you’re looking for someone to take over tasks that you find tedious. But don’t worry, people love all kinds of work. That’s why we have accountants who actually enjoy their jobs. And after all, that’s what you want for your business: everyone should love all the work they’re doing. That’s why you’re hiring. You’re giving people who crave certain tasks a chance to do them for you, for your business, and ultimately for their own enjoyment and livelihood.

Links I Found Interesting

The folks over at Stay SaaSy wrote about The Rogue Wave of Enterprise SaaS, explaining that when startups hit the Dunbar number of ~150 people, a lot of small problems consolidate into one big problem: the old processes start failing, the prior expectations of a small and agile company collide with the reality of a much bigger enterprise. The article explains the warning signs and how to prepare for it. Of course, rarely does a bootstrapped business grow to this size, but I am a firm believer in knowing what to prepare for, even if it’s unlikely to happen.

This Wednesday, the wonderful Tom Osman of Makerpad invited me to hold a Workshop called “Taking Your Business From Zero to Sold with Arvid Kahl pt.1 | Makerpad Workshop”, where I shared a few thoughts on NoCode, my book Zero to Sold, and answered viewer question. If you missed the workshop, here’s the recording. It was a really fun evening.

Recently, I asked my Google Home to set a timer for three minutes. It joyfully responded that it had successfully set a three-WEEK-timer. Just what I wanted! Took me another full minute to get my timer set up correctly. Voice interfaces are often quite frustrating. So it came as a breath of fresh air to read Ian Bicking‘s article called Thoughts on Voice Interfaces. If you’re interested in what people working on the technology are thinking and doing, this will be a great read. There is hope.

As founders, we have to become experts in many fields at the same time. This week, Laws of UX will help you become an expert in User Experience by exposing the fundamental laws of the field. From the Aesthetic Usability Effect to the Zeigarnik Effect, the website has in-depth explanations and examples that anyone building a user-facing product should at least have glanced at. Highly recommended. For an extra moment of questionable joy, read the Hacker News comments that consist mostly of people complaining about the UX of the Laws of UX website.

Finally, I ran into these stories that are not related to bootstrapping, but are still extremely interesting:

  • How A Cheese Goes Extinct: Both before and during the pandemic, cheeses sometimes vanish because their makers perish or stop making cheese. As a proud cheese lover, this article reminded me of how much knowledge and labor goes into the products that artisans create.
  • The earliest domestic cat on the Silk Road: It appears that the first house cats as we know them come from the Silk Road. Rapid urbanization along the heavily frequented trade route seems to have helped the kitties become more domesticated.
  • SpaceX says Starlink internet has ‘extraordinary demand,’ with nearly 700,000 interested in service: As someone who intends to live in a rural location quite soon, Starlink can not come fast enough. I am glad to see so many other people thinking the same.
  • An Inside look at CloudKitchens: As more and more restaurants are closing due to lockdown measures, cloud kitchens are thriving. The article gives an exclusive glimpse into the logistics of the co-working restaurants of the future. Very insightful.

Bootstrapped Successes & Failures

Adam Wathan, creator of Tailwind CSS, shared the story From Side-Project Byproduct to Multi-Million Dollar Business. What intrigues me to the most is the origin story of the framework that has blown away the competition: two abandoned side projects that went nowhere. Both built with what at the time was “just a custom CSS framework.” Tailwind was never intended to become Tailwind. And then the story of Tailwind UI, the moneymaker. It’s a technical bootstrapper’s dream come true, and it has been rewarded with $2m in revenue. Big congratulations to Adam.

Dylan Wilson published What I Learned About Failing from my 5 Year Indie Game Dev Project this week. He openly talks about failure, which is important for us founders to become comfortable with. His take on “failure disguised as success” resonated with me in particular. Things feel like they’re working, but they’re working against your overall goals. Recognizing your own blindness here takes strength and reflection. And, even with Dylan stopping to work on this particular project, we can find solace in the fact that he found the Indie Hacker community and the plethora of knowledge and guidance that will make sure his next project will work out just a little bit better.

Ben Birnbaum learned what happens when you find out you’re the copycat. His first thought was to just quit, but he reconsidered and vowed to continue working on his app Cortado to distinguish it from the competition. Best of luck Ben, hope you’ll find a good way to eventually monetize the product.

Steve McLeod (of talks about what happened when he raised his B2B SaaS’s prices in 2019 and then again in 2020. It looks like it’s working well for him and his project Feature Upvote: his customer base is shifting up-market, signups are climbing upwards as well. With a maturing product, you can afford to charge more. This is a very clear example.

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.

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,