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I've decided to do a crazy thing..
I’ve decided to do a crazy thing, and that is to quit my job without any tangible thing to keep me afloat – another job or a seriously good idea that is bound to make me billions..
I’ve decided to take “some time off”.
Even though I am calling this impending experiment a Bootstrap Sabbatical, let’s be clear, this is anything but a break. It is however a break from growing other people’s businesses and, rather, realigning myself professionally as an Entrepreneur.
I will nonetheless continue to advise and mentor the existing Startups, Accelerators, University Programs, Founders and Funds I am involved with – but with less priority.
For me this will be a year of focus, idea generation, innovation, execution, learning, growth, and actualisation as an Entrepreneur and business builder. It will also be about doing so publicly.
This experiment is based heavily on Jakob Greenfeld’s Bootstrap MBA, which I found incredibly refreshing and resonated highly with my personal aspirations of the moment – even if our goals do somewhat differ; Jakob is focusing on self-learning, I am focusing on building (even if Jakob is pushing out products at impressive speeds!).
What's the main goal here?
It is perhaps a result of a weird lovechild germinating in my mind through inspiration of Andrew Wilkinson and Chris Sparling’s Tiny Co. and the eccentric and enigmatic Felix Dennis’ How to Get Rich and John Warrillow’s Built to Sell that I have determined the following 5 year personal goal:
I want to own an umbrella organisation that is responsible for several profitable businesses, that are primarily run and managed by people other than myself.
What are your goals and the philosophy behind them?
The fundamental goal of this experiment is to build businesses and products quickly and regularly. Everyone has ideas (and I have many), but execution is what matters.
I pride myself on being a seasoned startup operator, so the goal here is to continue to narrow my focus on quick, but excellent, execution and the constant delivery and shipping of products.
An excellent idea done poorly does not make for a great outcome, but an average idea done excellently will likely still lead to an exceptional business.
I see this goal as the base for all others, and the ultimate purpose of my experiment, to continue releasing businesses and working on ideas until one sticks and shows potential for scale, then I double down.
You can invest all your money, get a blessing from a shaman, say a little prayer and throw one very well calculated dart, and still miss. Or you can throw 6 darts and you’ll likely have a better chance of hitting the bullseye.
Thus, the goal here is not to continue shipping products into perpetuity, but to find a business or two that have massive potential or that spark interest for continued perseverance.
ACTIONABLE GOAL: Launch 1 Business Every 2 Months of 2021
On a macro level, running a business is fairly simple algorithmically:
Your goal is to sell a product that people want, for more than it costs you to make, and sustain it. Then, repeat that over and over, with growth.
I’ve been involved in the startup scene for close to a decade and must acknowledge that we startup folk have sometimes failed to see the forest from the trees. “Growth at all costs” has been rife, and it has been perhaps the publicity of companies like SoftBank that have increased a sudden interest in the supposed ‘simplicity’ of self-sufficient solopreneurship and the pursuit of actual profit.
In line with this ‘trend’ to realise actual revenue and the pursuit of profit, the goal is to generate revenue from the businesses I create.
In order to measure value, one must capture it through charging.
Some of my businesses might not always follow this path directly, but I am making this goal to ensure I do not resort to old startup habits, including the failure to charge customers in the pursuit of users and “other” growth vanity metrics. If I go this “indirect” route, there should be a clear thesis of the business model and path to profitability. Not charging for a product should be a choice, not a result of an inability to capture value.
To refer back to my algorithm above, this goal is to ensure I am aligned and reminded that for an early stage venture, the growth of revenue, is the noblest of all growths.
ACTIONABLE GOAL: Publicly show revenue with the goal of hitting $100k or $10k MRR by Dec 31, 2021
Solopreneurship is lonely – I’ve walked this path before when I built Fiestafy – so it’s important to conscientiously keep a pulse-check on how you’re tracking.
I previously did this by attending at least one tech meetup a week. If I found myself pitching the same “I’m currently working on X” two weeks in a row, I knew I was moving too slowly.
This time around I plan on building more publicly, showing my metrics, writing up my methods, and speeding up my attainment of feedback as a means to stay ruthlessly accountable.
Furthermore, and importantly, I aim to grow my network, both locally and internationally, through this endeavour. I plan to do this via regular coffees (virtually and in person), hosting more of my Growth Dinners and through my writing.
To ensure this goal is not a vanity metric and to ensure the growth of my network is meaningful, I plan on collaborating on several projects for knowledge sharing and synergy, with the goal of finding an array of talented people I can team up with during the journey and in the future.
ACTIONABLE GOAL: Partner on a project with someone I’ve never worked with before by Dec 31, 2021
In order to hone my skillset in solopreneurship and startup scaling, I want to continue to gain knowledge in three fundamental areas:
Ideation
Execution
Selling
With ideation I want to focus on methods of idea generation and quick validation. I plan on doing this via studying some of the quintessential ideation books that I have yet to read and putting them in practice. I want to become an “idea machine”.
As a startup operations specialist, I want to focus on quick execution by continuing my learning of No Code and Low Code tools. I want to be able to continue my mastery of operational automation, as well as build quick but elegant solutions, with a good dash of doing things that don’t scale.
Later on, I also want to dive deeper into some macro execution knowledge on scaling in an effort to continue my learnings as a startup / technology business COO or C-level leader.
With selling, whilst I have an extended major in marketing, I want to refresh my skillset across the digital marketing landscape of the 2020’s. I want to continue my expertise in client relationship management and honing my direct sales skills. And ultimately, with the rise in interest of building, buying and selling small internet businesses like micro-SaaS, I want to learn more about buying and selling businesses.
Furthermore, to grow my network and become a better advisor, mentor and teacher, I plan to proliferate my learnings. Besides from doing, they say the best way to learn is to teach, so I want to formally ensure I am writing and teaching.
ACTIONABLE GOAL: Complete a course on no code / low code by June 30, 2021
ACTIONABLE GOAL: Publish 25 pieces of writing as means of education by March 31, 2022
ACTIONABLE GOAL: Sell or buy a micro-SaaS company by March 31, 2022
Let's lasso those goals and bring 'em on home..
To summarise, whilst there seems to be a lot here, I see all these goals as working together towards the master goal..
What's with building in public?
There’s something really special about launching a product or new business.
I’m not talking about the excitement of finally throwing your paper plane into the wind and seeing if it takes flight.
I’m talking about the fact that the audience have a vested interest. Even if they’re not buying your product, anyone privy to its existence plays a part in it’s fruition and outcome. And, what’s really interesting about human behaviour is that even though we love a movie filled of dramatical twists and turns, we usually rally for a successful outcome.
I’ve witnessed others, and to be frank, have been part of building in private, and, whilst there are times you don’t want to show your hand, building in public creates a sense of urgency, accountability and shared interest that generates both fear and enthusiasm that I am excited to try.
So, I invite you to explore my goals and share this journey with me, through the tribulations and the triumphs.
So that's it.. /TLDR:
I’ve quit my job to build several businesses and I plan to share the journey along the way.
I’ve got a whole lot of goals to keep me accountable, with the north star of working towards owning several profitable businesses by the end of 2025. Hopefully some of which I build myself during this experiment.
I acknowledge that planning and entrepreneurship is like mixing oil and water. However, whilst they don’t mix well, it’s better to have a constantly shifting form than none at all.
This plan is likely to change, and it should excite you that this is a story in the making, and I don’t even know the ending..
Come and join me?
I think this is going to be a wild ride..
To follow along on my journey, as I constantly try pick the destination, you can subscribe below:
Further, if you’d like to learn more about the Bootstrap Sabbatical, start your own, team up, or keep accountable together, I’d love to hear from you.
I’ll be Tweeting a lot about the journey, so make sure to follow: @kevjochelson
🙏 Thank you!
Thanks for taking the time to read about my journey.
If you want to find out what stage I’m currently at feel free to click here to visit my real-time goals: