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Photo by Jayden Yoon on Unsplash

Traditional logic says that all startups are high risk, and small software businesses are startups; therefore, small software businesses are high risk. From this conclusion flows the culture and system of fundraising that surrounds us, i.e. the water we’re in.

But what if we could show that many small software businesses — particularly SaaS, are not startups, but are in fact de-risked — albeit small, businesses?

We could lower the risk premium of lending to these businesses.

What good is a de-risked used-to-be-called-a-startup business with a lower risk premium? …

This post, written in the spring of 2012, chronicles the second chapter of our struggle to bootstrap a weather startup. With the disappearance of Tumblr, I thought it had been lost forever — but thanks to the Internet Wayback Machine, it’s been resurrected for your encouragement.

When I finished my last bootstrapping Stormpulse post, I had a strong conviction that the difficult parts of starting up were largely behind us — that we were finally on the ascent from the trough of sorrows to the summit of startup success.

How wrong I was.

As Eric Ries has said, the key to the hockey stick curve is the long flat part at the beginning. This makes sense — if we think about a hockey stick in the literal, the long flat part is where all the leverage comes from. …

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Photo by Ian Gonzalez on Unsplash

Data science is beginning to replace spreadsheets for entrepreneurs wrestling with uncertainty in their business models. How did we get here? What’s really new? And how can founders at any stage get better at predicting their future?

Staring into the Void

If you’re like most SaaS founders, you’ve googled for a financial template you can use to forecast your subscription business. As of the writing of this post, a query for “SaaS forecasting” returns 2.8 million results, many of them providing financial lessons and file downloads offering to help you see into the future.

Maybe you took advantage of one of these, at first; perhaps, eventually, you retreated to a blank spreadsheet — preferring an empty canvas of your own design over the learning curve of someone else’s formulas, or worse — macros. …

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. …

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Photo by Ross Findon on Unsplash

Riskpulse — the company I co-founded 12 years ago this August, recently announced a partnership with the largest managed services logistics firm in North America. With this, the analytic I conjured — the Riskpulse Score, or RpS (think, a FICO score for shipping) will be used to optimize the movement of tens of millions of shipments annually, or roughly $400B worth of cargo.

It’s a crazy thing, really. An idea imagined on my living room sofa — “what if … ?”

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Photo by Erol Ahmed on Unsplash

Previously, I described the new wave of funding sources that are emerging for bootstrappers. Today, we’ll place a fictional startup named “Array” under the microscope, consider a fundraising strategy, and compare the financial outcomes of raising money from three alternative funds based on publicly-available term sheets.

NOTE: This post was revised on May 23rd, 2019 using a new version of Summit that corrects the previous calculation of Earnest Capital’s “Founder Earnings” term. Thanks to Tyler Tringas of Earnest Capital for the clarification.

Imagine you have your very own startup: Array, a video conferencing tool for distributed teams. You have a real passion for the problem because you (like every other human), knows that every existing web conferencing solution sucks. Even better, you’ve already solved the real crux of it, which required rewriting part of the standard WebRTC library using C++. That means this idea is way out-of-bounds for most web dev kids-these-days. …

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Photo by Vishal Banik on Unsplash

Team and market are often cited as the two most important ingredients of outlier startup success. What do these really mean? What kind of team? And what kinds of markets?

Stories of successful distribution by upstarts are stories of exploited vulnerabilities in market incumbents. So it makes sense that growth specialists are called hackers.

Hackers & Painters, Paul Graham’s seminal tome of the Web 2.0 era, drilled the importance of the hacker ethos into early 2000’s startup founders. In short, at the core of hacking is rule-breaking.

The hacker label appealed to programmer lore, but its technical connotations belied the fact that the successful penetration of market defenses calls for more than programming prowess. It also requires grey-hat (rule-breaking) sales acumen, i.e. …

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Bryce Roberts ( & David Hauser (Grasshopper) discussing David’s un-VC path to a $150M+ exit.

Bryce Roberts of made the first stop of his 2019 Winter Tour at Capital Factory in Austin, Texas on Monday. What follows is an overview of the evening’s discussion which I thought would be helpful to share with anyone interested in the new wave of alternative funding that pioneered.

The v3 terms give us a new opportunity to tell our story. To remove uncertainty about what we’re doing and how.

— Bryce Roberts,


Background — 15 minutes
Founder story — from the trenches.
Live Q & A.


On the heels of this NYT piece (below), there has been quite a few reactions among investors & entrepreneurs…

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Photo by Hans Reniers on Unsplash

If market access is guarded by incumbents, how can unknown upstarts win? One common growth tactic is mimicking prior, successful attempts at gaining distribution. Founder stories get canonized, and eager disciples imitate.

But, vulnerabilities exploited by upstarts get patched. Success of the mission aside, Troy would be caught off guard by the pregnant wooden horse once and only once. The next Instagram will not be able to piggyback on Facebook’s social graph. The next Tweetdeck will not be able to use what’s left of Twitter’s API’s. The next Zygna will not be able to embed their games into Facebook. Each of these startups dove headlong into gaps that quickly closed behind them. (Good on them. …

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Not ordinary biplanes. (Credit: Transformer Toys)

Tremors, groanings, and the fat tail future of early-stage investing

For years, founder decision frameworks have pointed toward an approximate true North: growth. How do you know if some thing is the right thing? “Ask yourself if it creates growth. If so, do it. If not … why bother?”

The needle of that reliable compass has started bouncing lately. “Growth at all costs” has entered the zeitgeist as a pejorative. And as an opposite — but by no means equal, not yet — reaction to the growth hacker nation, a new wave of founders and investors have appeared. Their rallying cry? Sustainable growth through profits:

Even Paul Graham, author of the essay “Startup = Growth” that became an industry manifesto and rationalized VC funding for the sake of growth, is piling…


Matt Wensing

Founder, Summit. Believer in sustainable software businesses.

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