Since this is a book about breaking out of narrow constraints, there’s no tighter place to begin than the 2,100 square-foot Dutch Colonial on Laconia Road that me and my nine brothers and sisters were all jammed into. My parents turned the attic and basement into usable living spaces, but even with these renovations, we had to figure out how to shower every morning with only two full bathrooms. And there was a pair of kids to each bedroom.

It was in pairs that we grew up. Two girls. Two boys. Two girls. Then two more girls. And lastly, two more boys: me and my younger brother Mike. Mike and I got the smallest bedroom, since we were the youngest dyad of the crop. And that room wasn’t much bigger than a peapod. But Mike and I were so close that we didn’t need a lot of space between us. We’d often lose ourselves for hours playing with cars: Matchbox cars, Hot Wheels, Fisher Price and Tonka trucks, cars we built from LEGOs, a go-kart that Dad bought at a deep discount at the Auburn Sears & Roebuck because it had been sent to the wrong store, even real cars that we probably shouldn’t have been driving at ages 13 and 11.

During the 1979 oil crisis, Mike and I set up a toy gas station on our front sidewalk and lined up every little car and scale model that we owned. There must have been close to 100 cars, including the last one in line, which had a to-scale handwritten sign on its rear bumper that read, “Last car in line. No gas.” The Worcester Telegram came by and got a photo of the Vassallo fleet. The caption described Mike and I as, “Playing for Real.”

Steve (front) and Mike in the Worcester Telegram.

A lot of people have similar stories—albeit with fewer siblings usually in the mix. What sets people who grow up to be designers apart from most others is that they wanted to keep playing. I’ve heard it time and again from prominent designers, like Evan Sharp and Ben Blumenfeld, that when they were kids, they didn’t know that being a designer was an actual thing. They simply liked using their imagination to make stuff (very often with LEGOs). When they look back at their childhoods what they see in the distance are….Those drawings I made for my grandmother….That summer I spent teaching myself to bind books….The Mac II that I wrote my first program on….That Big Foot monster truck model I didn’t think I could build, but did.

This elemental compulsion is what and who I mean when I say “designer.” Not necessarily someone who’s been classically trained in the fine arts, or industrial, graphic, or user-interface design. I wasn’t. But more liberally, anyone—even if they might not call themselves a designer—who has designed, built, and shipped things. These are people who have lived among the tools; who have experienced the deep satisfaction of refining the smallest details of something to an exacting finish; who know the pride and suppressed glee of finally unveiling a completed work to the world—even if the population of that world numbered just one person—and saying, “I made this (for you).” As they grew up, their childhood inclination for making things only deepened. And then, at some point, like magic, the world started giving them money, health benefits, and a 401(k) to be this way.


At least it felt like magic to me, when I rode that go-kart all the way from Worcester, Massachusetts into a job as a product designer at IDEO. There, I got to build everything from furniture and sunglasses to bun toasters and anesthesia-delivery devices.

After a long stint at IDEO, I went on to do other things, including start companies, and somehow along the way I wound up as an investor. But I still build products on the side and sell them on Amazon. My idea of a fun weekend is finding bespoke manhole covers to give as gifts, or helping my six-year-old daughter build a 2700-piece, 1:8 scale LEGO model of the Porsche 911 GT3 RS. I could talk about the kinematics of the machine I built in grad school for folding and launching paper airplanes until there’s no one left in the room to listen. I’m a designer who happens to be a venture capitalist.

Steve’s daughter – the next generation of Vassallo car nuts?

Fortunately for anyone belonging to this unbearable tribe of nitpicky craftspersons, this is an amazing moment to be a designer. In recent years, design has come into its own as a competitive lever for businesses, as a set of practices for solving important problems, even as a method for optimizing your life. Design thinking is being taught to kids in some primary schools. Across industries, companies are trying to infuse their organizations with design sensibilities. And if you’re a talented designer in Silicon Valley, the work finds you.

There’s a subset of designers, however, who’ve started to wonder if there isn’t something more they can do than pure craft. If there isn’t a bigger impact they could be making on the world. These young women and men look to the designer cofounders of companies like Pinterest and Airbnb and they wonder if—and how—they might be like them. But they feel boxed in by ignorance or trepidation. Or they’re lost at sea as to where to begin.

I remember the feeling well. I loved and still love designing products, but after a half decade at IDEO, doing only that felt as constricting as that tiny room with the bunkbed and one small desk that I shared with Mike. I knew that I wanted to do more. I was lucky and eventually figured out a path, even though at the time there wasn’t much guidance out there for designers who wanted to become entrepreneurs.

Unfortunately, when I survey the landscape now, there’s still not much help for young designers. There are reports filled with statistics about design—LinkedIn stats about designers in tech, numbers on designer-led startups, M&A activity of design firms, and fragmentary analysis of the design ecosystem. Industry observations. But there isn’t much substantive insight about what’s required of designers to become successful founders, gleaned from the frontline stories of those who’ve lived to tell the tale. I wanted to do something about this void, and I decided to approach the problem as a design challenge.

For anyone belonging to this unbearable tribe of nitpicky craftspersons, this is an amazing moment to be a designer.

As a product designer-turned-entrepreneur-turned-investor, I think that design is non-negotiable for building the great companies of the future. I want to help designers who want to become entrepreneurs and entrepreneurs who want to create design-empowered organizations. So, like any good design thinker, I started off by forming a research team, to explore the real-life stories of design entrepreneurs. Over the past nine months, we interviewed scores of designers, design scholars, and most importantly, designer founders—including the cofounders of Pinterest and Airbnb. We set up a war room at Foundation Capital to analyze what we collected. We held mini-design sprints and prototyped numerous versions of what you’re reading in myriad forms. All in an attempt to plot the trail signs and marker-buoys of design’s terra incognita—how to go from designer to designer founder. What follows is what we learned.


This work is intended for entrepreneurial designers, for designers who want to know more about what it takes to start a company, and for non-designer entrepreneurs and executives who want to understand how to make design a core value of their business.

After reading this, some designers may decide that becoming a founder is not for them, and there’s no shame in that. But for designers who are thinking about undertaking the entrepreneur’s journey, I want you to know what will be required of you. I also want you to know that there has never been a better time in history to be a designer with grand dreams. You might not know it, but you have it in you to do impossible things. You can take your designer’s brew of creativity, curiosity, and an incurable itch to improve things—and use it to elevate the way people live. You can use your mutant powers to transform— for the better—how we travel, eat, take pictures, share, collect, connect, cure diseases, vote, love, create. You can play—for real.



A Creative Expedition

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