Category: SaaS
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The Guide To Bootstrap Funding
Money is tight in the early stages when bootstrapping, before there’s any significant revenue in the company. Once you reach around $1M in ARR, you start to experience what I call the “SaaS escape velocity” – most normal business expenses are now a much smaller % of your revenue, and you start to feel more…
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My Product Ideation Framework For B2B SaaS
A common question I get from aspiring founders, is how to find and then validate product ideas for new B2B SaaS products. Over many such calls, I started to flesh out a mental model for how I would approach coming up with a new product idea for B2B SaaS, and I use this framework when…
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How I Bootstrapped a B2B SaaS to 7 figures in ARR
(and an 8 figure exit) In 2016, after winding down a failed startup that went the VC route, I had $15k in my checking account. I had just moved out of the SV bay area to reduce my living costs. My goal was to stretch this small amount of money as far as possible, while…
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From LOI to close – Navigating the sale process
Everything I learned going through an 8-figure business sale – from LOI, to due-diligence, legal documents and closing.
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The bootstrapped founder’s guide to selling your company
There comes a time in the life of most successful software businesses when the opportunity to sell the business becomes available. This is especially true for income generating, subscription SaaS businesses, which are a prime investment for various acquirers. 2 years ago I started receiving inbound inquiries from various investors asking about a potential acquisition.…
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The 8 Best Marketing Channels For B2B SaaS
When I started Gymdesk in 2016 as a solo founder, I had high confidence I could ship a working product, but much less confidence in my ability to generate demand and acquire customers – i.e, marketing. Over the past 8+ years I had to learn how to generate leads and convert them to paying customers…
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Bootstrapping Vs VC Funding – Pros & Cons
From 2010 to 2024 I started 2 companies – one was VC backed marketplace startup, which raised a seed round but ended up fading away after running out of money, and the other a bootstrapped B2B SaaS which I grew to 7 figures in ARR and an 8 figure exit without VC funding. In this…
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How to fire yourself as a founder
In my previous post I wrote about the process I went through growing Gymdesk from a one-person operation to a company with over 10 FTE at that point in time. One of the least expected outcomes of this process was that hiring more people did not reduce the amount of work I needed to do…
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Building A Fitness Tech Company During COVID
In my previous article I stopped just before things got interesting. Gymdesk (then Martial Arts on Rails) had reached $12k in MRR in the middle of 2019, then remained stagnant for the rest of the year. $12k / month was enough for me to quit my full time job and dedicate my full attention to…
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Bootstrapping to Profitability, the story of a B2B SaaS founder
When I started building Gymdesk at the end of 2015, I had no idea how long it would take for it to be profitable enough that I could live from it full time. At previous companies and roles I had primarily been the technical founder / lead, focused mostly on building the product and underlying…
