On April 14th, 2019, I shared that after 15 years of starting up, I was ready to start something new. Today, I’d like to share the reasons behind my decision to join TinySeed’s first batch of startups.
When I began coding my first startup in 2004, Paul Graham’s Hackers & Painters had just hit the shelves of Barnes & Noble, acceleration meant moving to the Bay Area, and few to none would argue the viability of being a solo founder. In that environment, my journey from Florida-based founder with a family to CEO of a successful enterprise SaaS business was filled with friction.
Emerging fifteen years later to start anew, I rub my Rip Van Winkle eyes and am delighted at what I see. The world has learned that much of the headwind I faced previously was, or at least is deemed, unnecessary. Much has been said and written about the improved tooling of SaaS — there’s now a SaaS for almost every challenge of building a SaaS, but even better and more recent, the capital stack has also matured.
In 2008, halfway though my previous trek, Paul Graham wrote in his “High Resolution Fundraising”:
Different terms for different investors is clearly the way of the future. Markets always evolve toward higher resolution.
With the rise of convertible notes, SAFE’s, and other standardized terms, this vision has been made manifest.
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But even more importantly for me, different terms have finally emerged for different ways of life. “Startup funding for the rest of us” is a feature of the landscape that I didn’t even know I needed the first time around. Now it’s here, here, and here, and in later stages, over there too.
The fertile substrate of this Spring is the fact that, for many of us, the lines between the personal and professional are obsolete. Not because one must wither while the other grows, or an acceptance that one will inevitably choke out the other; rather, because the thought of sacrificing one for the other is nonsense. We don’t have to choose. I already see this among this batch: a group of founders, investors, and mentors reaping the tangible and intangible rewards of working with the flows of their own energy and values.
Yes, the seed stage is a promising time. But all the more so, given that my mission with SimSaaS is to help us — founders and investors, select from many possible futures — futures where the financial and personal are often unabashedly commingled, I’m especially eager to prove, along with my new traveling companions, that the best futures will follow from each of us doing our work, for our reasons.
TinySeed is a 12-month program. You can follow my year-long journey building SimSaaS right here, or on Twitter @mattwensing.