Snowed in here in Connecticut today. Good day to reflect.
Last week we had a quarterly board meeting⦠and it had me thinking about the people around that virtual table.
My exec team. My chairman (who started as my first and most trusted advisor). Board members from our investors. A few observers. When you zoom out, itās kind of surreal.
Bootstrapping is hard. Fundraising is harder... especially right now, when VCs are comparing everything to AI companies posting absurd year-one growth numbers⦠or writing big checks into pre-revenue, pre-PMF AI dreams (hallucinations??).
And even if you raise successfully, money is just money. It only gets you so far.
The real variable is who you partner with.
VCs come with capital... but also ops teams, recruiting help, experienced pattern recognition, and networks that can open doors you simply canāt on your own. Choosing a firm isnāt just about terms/valuation. Itās about alignment.
Are they active or passive? Are they the kind of partner youāre nervous to bring hard news to⦠or grateful to have helping your through it? Do they truly understand your model and ethos (eg: OSS, dev tooling, exit ambitions)? Have they actually lived it as operators?
If theyāre leading your round, theyāll likely take a board seat. That means real influence over your projectās future.
Are you choosing a firmās logo⦠or their specific sponsor? What happens if your sponsor leaves the firm? Do they want growth at all costs... or responsible growth?
More importantly⦠which do you want?
A few years ago, I knew literally nothing about any of this. No MBA. No playbook. No ChatGPT. Just a design degree, some light technical skills, and an equally capable, excited, and motivated co-founder (hey Rijk!! š).
YouTube got me started, haha... but my investors helped me actually grow into my role as CEO.
Thatās why it matters who you team up with (in business and in life).
It can feel like you should jump at the first term sheet. Maybe sometimes you should... survival matters.
But these are long-term relationships. Do your diligence. Ask them for references. Talk to their founders (not just the successful ones).
Five years after converting our OSS project into a DE C-Corp and raising a $1.5M SAFE (microscopic by todayās standards)⦠I still feel great about those early choices.
Yesterdayās meeting was long. Some topics were more controversial. But it was honest dialogue around things that mattered, it was about alignment, and it was respectful and exciting (from what Iāve heard, this isnāt the norm). And thatās not luck.
Iām extremely grateful for Handshake Ventures, True Ventures, F-Prime, Eight Roads, and PWV (Preston-Werner Ventures). Not just for their initial trust, but for their ongoing support in this shared vision of Directus.
Capital helps you grow. The right partners help you build something that actually matters.