Hi friends,

Welcome to the first edition of my newsletter! I'm thrilled to have you here. With so much thought leadership out there, your support means a lot.

🤔 Why am I Writing This Newsletter?

As I’m transitioning between tours-of-duty, it’s the perfect time for me to reflect on some lessons I’ve learned in my most recent experiences.

My main goal is to use this platform as a rubber duck as I write out my experiences to learn from them. The very close second goal is to help all of you avoid some of the dumber mistakes I’ve made! 😊

I’m doing this as a closed newsletter to ensure I can write openly about my experiences. While I'll share candid insights, I will respect confidentiality agreements, so don’t expect any gossip here—and assume some details and exact numbers to be reasonably obfuscated.

📈 A Tale of Two Cities Startups

For context, here are my last two tours-of-duty, each serendipitously lasting 2 years and 7 months.

• Teachable (06/2019-12/2021): A commerce platform for knowledge entrepreneurs / creators that I joined around $15MM/y and guided through the pandemic, a very successful strategic acquisition, and 4x growth to $60MM/y.

• Workstep (01/2022-08/2024): A 2-product B2B software company that I joined at ~$10MM/y, scaled down to ~$1MM/y and then scaled up to ~$5MM/y. Sound like an absolutely crazy thing to brag about? I’ll share later why this was an amazing strategic unlock for the company! Also, this isn’t exactly true, but makes for a more interesting story. 😎

These tours were at the same time incredibly different (serving digital native solopreneurs and serving some of the biggest companies in the world with their massive frontline workforces—kinda not the same!), but also…very very similar.

As unique as an individual company’s path may be, depending on a dizzying number of factors (product type, market / customer type, vertical, go-to-market strategy, funding model, exit goals etc etc), its core journey forms very common patterns with others.

🚶‍♀️ What is “Startup Adolescence”?

I started my obsession with a specific part of this journey back when I worked at Produx Labs, serving the Insight Partners portfolio: the “adolescence” of a company: That weird middle ground between “startup” (a company searching for product-market fit) and “scaleup” (a company exploiting established product-market fit for rapid growth towards portfolio expansion and exit).

This stage of a company is overlooked in traditional leadership lore and ignored as an area of specialty. The internet is filled with guidance on how to incubate a new product, and an abundance of talent / consulting exists for establishing mature, fully scaled out enterprise organizations.

Meanwhile, the transformation between the two is either completely ignored—or even worse, trivialized as a linear set of steps of overnight change from immaturity to maturity.

That’s just not how it works—and this ignorance is a common driver to why so many great companies hit a brick wall of growth around the $5-20MM/y mark. What got them here, won’t get them there.

This is why I love the “adolescence” analogy: just like the human teenage years, a company transforming from startup to scaleup is a painful, multi-year, non-linear, confusing, frustrating, exhilarating journey. Going from the opportunistic and risk-hungry hustle+grind of the early days to the thoughtful and deliberate strategic brush strokes of the growth stage is wrought with peril. There equally many dangers in not maturing fast enough and maturing too fast.

📚 What you’ll read about in this newsletter

Ok, the framing above is set—where’s the beef?

Consider this first installment as a statement of intent and a menu of the meal to come. Below you’ll find a non-exhaustive list of topics that I’m itching to write about.

But consider this as much a menu as an invitation: let me know which ones whet your appetite and which ones make you let out a big ol’ “meh”. I’d love to receive email or have this form filled with your preferences out of this grab bag to guide my hand!

• The “more-is-more” fallacy—how premature expansion kills great companies and how 9 times out of 10 the right strategic unlock is getting the whole company building on your core strengths.

• Most problems are leadership team problems—so far I haven’t run into an issue with a startup transitioning to a scaleup where the most leveraged solution hasn’t started from the leadership team.

• However much time you think you have, you have way less—I hope you’re already familiar with Ben Horowitz’s concept of “wartime / peacetime CEO”—the funny thing is, I’ve yet to see a startup-to-scaleup transition that isn’t effectively 100% wartime.

• Working with, for, and around founders is a real skill—I’ve been super lucky to work with exceptional founders only. But the exact skills and traits that make someone an exceptional 0-to-1 founder usually make them terrible 1-to-10 operators. Despite them always being some of the smartest and hardest working individuals you’ll ever meet.

• Exploit-vs-explore in this stage usually needs to bias for the latter—most product people’s instinct is to solve all problems by building more. This is one of the stages of a company’s journey where empowering other parts of the org really pays off!

• There is no “product strategy”—It’s all company strategy? Always has been.

• You need to get better at firing—Sad topic and as much of a note-to-self as a tip to anyone else. It took me like 2 decades to realize that often the best way to improve a team is to remove people, not add.

• Navigating the “ruh-roh we need to rebuild everything” issue—I’ve yet to find an early growth stage company that isn’t facing challenges where a full-blown rewrite seems like the only way out.

• Venture capital as an operating environment—you can’t play the game if you don’t know the rules governing winning or losing.

• Enterprise SaaS—whoo doggy, that’s a different-a meat-a-ball! A lot of my preconceived notions of “great product work” looked like were thrown in the garbage when faced with a high ARPC / low customer count environment.

Ok, I’m going to stop here. I hope you’re getting enough of a whiff of where my mind is at with this “curriculum”. Disclaimer: I do reserve the right to skip any topic above and randomly add others.

❗️ Plz Halp!

As we get going, here’s a few things you can help me out with.

💌 Please drop me a line via email or give me feedback with this form so I can make this newsletter better for you—happy to take requests on topics or answer more specific questions in the privacy of a 1:1 conversation.

📩 Forward this email to someone you feel would get value from it—or direct them to https://startup-to-scaleup.beehiiv.com/ to get them in the secret gang 🤫!

📆 Get on my Calendly if you really want to chat.

🤝 Intro me to your favorite startup CEO that is looking to scale or VC/PE fund operator that has parts of their portfolio needing a spruce-up.

Excited to be back in writing mode!

Tommi
forssto.com