Bootstrapped startups and the shit I learn in therapy

When I think about my vision for the future of Krit, the next two years come easily. By the end of 2021 we want to:

  • grow our team from 8 to 20
  • hit $2 million a year in revenue
  • continue to make Krit one of the best places in the world to work
  • launch 10 new products that make a huge impact on the lives of their founders and customers
  • build a strong reputation as honest developers, creative designers, and disciplined product managers
  • grow our reach online by 5x

A few of my more specific, actionable goals include:

  • launch a book, course or workshop
  • increase R&D time
  • improve benefits (401k matching, better healthcare coverage)
  • introduce sabbaticals
  • establish an apprenticeship program
  • set up a fund to support diversity & inclusion in tech

In the last year, we've made huge progress. We added Karen to help us shore up operations as well as Austin and Jess to work on front-end projects. We had two pieces of content go viral, had our most profitable year ever, made tough decisions about the right kinds of clients to work with and drastically improved our project management process.

Tomorrow we'll hold our first in-person retreat and spend 3 days reflecting and enjoying being together. There are always more areas to improve, but we are set up well to grow and hit these 2-year goals.

But when I start thinking 5 years out, everything gets a lot murkier. This is due, in part, to the Lindy effect. Written colloquially the Lindy Effect states that "however far you are, you can likely double it.

However far you are, you can likely double it.

It's easy enough imagining growing Krit from 8 people to 20 or from $700k in revenue to $2m. We do what we've done so far again (plus a little extra). But thinking beyond that requires a shift in mindset and strategy.

So I've been asking myself a series of questions, to help frame the discussion (you don't have discussions with yourself?). With some questions I'm trying to think beyond 5 years, but still with the goal of informing my 5-year vision for Krit.

  • What can we realistically become the best in the world at?
  • What do we actually give a shit about?
  • What factors aren't going to change in the next 20 years?
  • What does enough look like for us?
  • What can we do differently to get to 10x without growing 10 times in headcount?
  • What will we most regret not doing if we're looking back at age 80?

What can we realistically become the best in the world at?

We are uniquely good at building Minimum Loveable Products, a skill that sits at the intersection of product management, design and development. If you remove any one skill, we're not as strong. Our design strength is that we understand the development process and vice versa.

We're also excellent at team building, specifically hiring developers. It gives me a ton of pride that our team is full of kind people who don't fit the common developer stereotypes.

What do we actually give a shit about?

We won't ever be world-class at something if we don't care deeply about it. The things that spark our joy are:

  • Design that looks great and serves a purpose
  • Building a healthy, inclusive culture
  • Giving people opportunities to get into tech and grow in their careers
  • Educating and connecting with an audience
  • Using our knowledge and skills to create a new product from nothing
  • Making a positive impact on the world

What factors aren't going to change in the next 20 years?

We are building a lasting business. This means we need to consider how different the world may be and be willing to adapt over time. But while it's incredibly difficult to predict trends, it can be easier to predict what won't change. These then become the bets that we build our business on.

There will be more software in the world. Now that software is here, it isn't going away. People want their lives to be easier, and so automation will continue to grow. It may look different, and will almost certainly be built in new ways we can't imagine, but there will be exponentially more software in 20 years than there is now.

People want software to look good and be easy to use. No one will ever say, "I wish this product was ugly" or "this is too easy to use." In other words, it's worth investing in good design. As a skillset, a market position and in our own products.

People will continue to create new businesses. Creating new businesses will still be one of the best ways to generate wealth, build a good lifestyle and make an impact on the world. In a way, this is a bet on capitalism and its ability to weather the societal challenges it faces today.

I considered adding that people will want new software to be cheaper, but I don't know that this is true for us. As long as we are selling a service, then price factors into people's expectations and our market position.

What does enough look like for us?

There isn't a revenue number, a number of employees or some other metric that will mean we're done. This isn't a finite game, but we also don't want to get stuck in a self-defeating hustle loop. We don't want to be working ourselves to death or missing the great parts about where we are today.

Consistent growth is an important part of our "enough." We're not happy sticking to the status quo. But we don't need or particularly want rocket ship growth either. For Krit, enough means:

  • The financial freedom to pick and choose our projects and partners
  • A safety net to let us take on new risks and challenges
  • Above-average pay for everyone on the team
  • Above-average time off and benefits (benefits, not perks)
  • Steady and consistent growth, both personal and financial

What can we do differently to get to 10x without growing 10 times in headcount?

Right now, the idea of growing our headcount by a factor of 10 isn't appealing. 10x-ing our team would likely mean introducing bureaucracy and structure that would make the work we do a lot less fun. If nothing else, we would have a lot less flexibility.

So how do we get to 10 times the revenue and/or the impact?

We have to increase the leverage we have on our time. This means productizing our services, raising rates, introducing workshops and info products, taking on more risk (investing in companies) and/or launching software products of our own.

What will we most regret not doing looking back at age 80?

When Jeff Bezos has talked about starting Amazon he talks about the regret-minimization framework. Rather than optimizing for success now, he imagines being on his death bed reflecting back on life. What would he most regret at that point in time?

This is possibly the most personal of all these questions. My answer comes in two parts.

  1. I would regret not swinging for the fences at least once. I think at some point I will want to take a big swing and try to create something that shakes up the world just a little bit.
  2. I would regret working too much. At the same time as I want to swing big, I believe relationships and experiences matter more than work or wealth. It's not worth swinging big if it means sacrificing personal health, relationships or that we postpone experiencing this crazy world we live on.

So what? What does all of this mean? Where will Krit be in 5 years?

5 years from now we will still be working with clients, but our reputation and audience will have grown significantly. Our team will be more skilled at positioning ourselves, and we'll have deeper knowledge of our ideal customers.

Getting there will take a balanced approach of conventional growth, and reinvesting in ourselves all while maintaining profitability.

We'll use our audience to sell knowledge products like books, courses, and workshops. This will in turn help to build our reputation as experts in the field. Productized, strategic consulting will be a larger part of our service offerings and we will command higher rates while being more selective with clients.

Our team will be more diverse than ever, and Krit will consistently be recommended as a great place to work. Our pay and benefits will set the standards for what is possible with an agency.

Within the next 5 years, we will take at least one big swing. We will either partner with another team or entrepreneur to build a product or build a product of our own. This product won't replace our service work, but rather give us a fresh outlet to hone our skills. If successful, we'll spin it out into a company of its own with a small team to grow it as a separate business.

We have an incredible opportunity. Our reputation is strong, and our team is one of the best there is. I'm excited for the journey.

P.S. I recently found this picture. I filled out this post card more than 5 years ago at an event where I heard Alexis Ohanian speak. A year later I started Krit with the help of my friends Austin and Bill.

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