Mentoring B2B SaaS founders

I grew Gymdesk from 0 to $3M in subscription ARR and an 8-figure exit over the course of 8 years as a bootstrapped solo-founder.

Through this process I evolved from a technical founder to a well rounded operator and a product expert, unlocking the ability to drive consistent growth to the business while remaining lean and profitable.

I learned an incredible amount during this time, and developed the soft and hard skills necessary for a repeatable B2B SaaS growth journey. If I knew what I know now when I started, I’m confident I could cut the ramp up time in half and have an even better outcome.

I still enjoy the high level part of growing a B2B SaaS company. I’m still learning and evolving as we are going through the scale-up phase of our company, and working closely with our private equity partners.

As I gradually reduce my involvement in Gymdesk post-acquisition, my focus is now shifting to mentoring early-stage founders and help them get over the hump and on a strong growth trajectory, all the way to a life changing outcome.

Mentoring Founders From 0 To Exit

There are many paths available to founders who are looking for outside help – from raising VC or angel funding, to joining an accelerator or an incubator.

We went through the TinySeed accelerator with Gymdesk, and for me the biggest benefit was getting to work 1-on-1 with Rob Walling (TinySeed partner, previously exited with Drip), and relying on his experience navigating a few critical junctures in our company’s journey, such as redoing our pricing strategy or hiring our CTO.

I’m now sharing my insight and experience as a SaaS operator with founders in every aspect of growing a B2B SaaS company:

  • Growing a company while bootstrapped and with limited resources
  • Go-to-market strategy (Marketing / Lead-gen / Sales / Onboarding / Customer Success)
  • Product strategy and building a PLG (Product-led-growth) motion
  • Pricing and payment strategy
  • Internal and external team building and management
  • Developing new acquisition channels
  • Building out a holistic payment strategy for adoption and revenue
  • Preparing for an exit and going through a successful sale process
  • Everything else I can help with!

What I’m Looking For

I receive a lot of inbound from people in different stages of their journey, and as much as I would like to help everyone I’m trying to focus on where I can provide the most value.

  • You should have a live product – I have a few articles on ideation, but I’m not the person to help you find an idea and build your MVP
  • It is a B2B SaaS product – B2C and non-SaaS products require different skillsets and approaches
  • The product is generating at least $1000 in MRR (monthly recurring revenue) – Showing there’s businesses who would be willing to pay for it
  • You are (mostly) bootstrapped, and are not looking to raise VC funding (at least in the short term)

My Mentoring Engagement / Investment

As a mentor, I’m there to help you think through difficult / ambiguous decisions and tackle issues in your product and company. I remember full well the level of uncertainty and anxiety that is part of the daily grind as an early stage founder.

The process we will go through is as follows:

Stage 1: “Dating”

I start every engagement with a few weeks of joint work, during which we get to know each other better, and both sides get a better view of how an ongoing relationship would look like. I help with a few initial issues you would like to tackle, and you show me you’re able to execute on small projects we decide on together.

Stage 2: The Proposal (Term Sheet)

If we mutually decide that it’s a good idea to add me as a mentor to the company, I will send a modified SAFE term sheet outlining the proposal.

  • I’m looking to obtain a 10% equity stake in the company (similar amount to the equity most accelerators take).
  • I will invest between $50,000 and $150,000, depending on the number of founders and stage of the company
  • The term sheet mainly differs from a standard SAFE document by outlining a conversion scenario (from SAFE to actual equity) based on a revenue milestone of $2M in ARR. SAFEs are normally intended to be used as a precursor to a priced VC funding round, but for bootstrapped companies that is not relevant, and this addition is for that scenario.
  • I provide mentoring availability of up to 4 hours / week. This includes: a weekly scheduled meeting, ad-hoc Slack and email communication on issues that come up, and on-demand calls when there are special needs, as well as any other research / materials I’ll prepare for the company.

The term sheet is fully annotated in lay-person language, however you are highly encouraged to obtain your own legal counsel to go over it.

Stage 3: Ongoing mentoring to help you reach your goals

Whether it’s building a long-lasting profitable business or reaching a life-changing liquidity event, I will do my best to draw on my experience to help guide you to your goals.

I believe that every founder I engage with will have success without me, and my goal is to amplify that success and shorten the time to get there, as well as reducing the anxiety and uncertainty that are so pervasive at the early stage.

We will engage on weekly calls, ad-hoc emails and Slack messages and condensed workshops to work through all the struggles and uncertainty you encounter on your journey to grow your company.

Sounds Like A Fit? Let’s Talk!

If you’ve read this far and this sounds like a good fit, please reach out and let’s talk! Even if a structured mentoring / investment does not makes sense now, I’m happy to discuss and try to help as best as I can.