they tell you not to invest in your first year of venture — or at most do one. the conventional wisdom is to observe, not be tempted, develop a bit of pattern recognition, and eventually, when the right opportunity comes around, you’ll be ready to lean in. well, that sounded boring to me. i’m too impatient for that, it seems, and it’s hard to temper my excitement when i get to meet new technical teams every day. of course, i have the unfortunate task of saying “no” quite often, though even i’m surprised how fast the first “yes” came.

back in december of 2011, i had just joined kleiner perkins and had a slew of meetings, coffees, and phone calls. it was exciting, overwhelming, not to mention i was swimming in a sea of new introductions generously made by friends and colleagues. during one of those 100 initial meetings, someone suggested i meet this guy — sahil — who just left pinterest to found his own payments company. that certainly caught my attention. luckily, my friend followed up with the introduction and i was able to meet sahil. i remember being a little shocked at how young he was (19), but also impressed how mature he was and his thoughts on design and business. at the end of the first meeting, we decided to keep in touch, began emailing about product ideas, and i tried to help him with some introductions to various valley companies for his partnership ideas. through those interactions, i quickly learned sahil was no kid — he was a force.

so, i started to dig into his product, gumroad. he’d raised angel funding, and the company was formed from one of sahil’s many side projects. this was a different type of product. rather than raise money for a specific idea, sahil saw a need earlier and just hacked together a tool to solve the problem of selling online. with gumroad, now links become vehicles for purchases. i dug around some more and saw that gumroad was in the luxurious position of having mostly organic traffic (which is priceless), and since i just came from twitter, the prospect of innovating around links was simply intriguing. i started to get more hooked on the idea.

founder, check. product, check. but what about market? this is tricky. it’s not a space i’ve poured over, but luckily, one that was clearly emerging. kp is already invested in square and has experience with other payment technologies. and, there’s the reality of what facebook and twitter mean to the social web. we all share links, billions a day. what if those links are just a way to get new content, sell items, buy e-books, sell instagrams, and so forth? during my runs over a few weekends, and it began to dawn on me just how big this market could be, and how close to the transaction gumroad could be. it was a simple yet powerful idea. the timing is right. the focus of “making selling as easy as sharing” feels right.

and so, i talked to my partners, and called up sahil and said i’d like to offer him a term sheet. i think he was surprised. there was silence on the phone. he wanted to think about it. that was fair and over the next few weeks, we talked a lot [and went up to sf to hack on a project together!]. there were some tough negotiations. this guy can negotiate! i’d be lying if i said i know where gumroad is going to go in the future. and, that’s the exciting part. i thought a lot about sahil, the product, the market — and making my first real venture investment. and, this just felt right. so, i followed my intuition after that, and was lucky enough to have sahil agree. it is a real honor to work with him, and i look forward to helping him and bryan, sid, and the rest of the gumroad team invent the future.

over the past decade, things moved really fast – sometimes too fast. founding a company – seems like a long time ago. at palm and twitter, things moved lightning fast. i figured that when i moved over to venture, it would still be fast, but not as fast — and i was wrong. only a few months in, and it’s moving really quickly. it’s exciting, but i also have to force myself to stop every now and then, to reflect, and readjust as needed. colleagues and friends have told me it could take a few years.

coming to this blog will be one of those forced “stops,” where i give myself the time and space to simply write, share, and ask questions. today, given how quickly things are moving, i wanted to stop and do something different — to write a letter to the mike abbott of the future, something to memorialize what i’d hope i could turn into as an investor — perhaps something i’d write now, tuck away, and read a few years later. so, here it goes…

dear mike,

if you’re reading this now, you’re probably on a caribbean island celebrating your second investment that has just gone public.

just kidding! never. i know that you are still hacking away. you know that, as long as you are uncomfortable, that you are learning.

you’re continuing to do the work that you love — plainly, to scour the earth to find captivating technologies, markets, and teams. you’ve had to say “no” more often than you’d like to, and it’s not easy, but all the “no’s” make the one “yes” more certain.

you’re a technologist and engineer at heart. you are drawn to technologies, both in software or hardware. there will be opportunities in other areas too, and you’ve kept an open mind when needed. you’ve also thought about markets. you’ve realized that, no matter the technologies in front of you, market sizes matter. yet, at the same time, there are moments when entirely new markets are created. you can’t afford to miss those, mike! and sometimes, disruption occurs not from a direct attack on a market, but from cutting in from the edge. keep your eyes wide open.

and, then, there are the entrepreneurs themselves: the founders, the founding team, the core engineers and designers… what it’s really about. it’s cliche, but “team” matters a great deal. you’ve gone to war many times with different teams, so you’ve been careful about who you surround yourself with, and you’ve guided your entrepreneurs to learn their own way, too. you’ve learned from your own experiences that ideas and tactics often change, but teams remain mostly the same, so you’ve invested in team-building and recruiting for the right attributes.

hopefully, too, you’ve learned that things don’t often present themselves as they truly are. you have to be both optimistic and skeptical. you’ve come to your own conclusions, paying little attention to what the chorus may say. you’ve learned to really use the products and services you decide to invest in. and, you’ve given careful consideration to the teams and products that don’t look normal, that may be true outliers. you’ve been unafraid to lead, or to back the un-backable. you haven’t needed validation when you’ve decided to lean in — it’s a choice you’ve come to naturally.

and, finally, there’s work, and there’s life. you know you could work 24 hours a day, 7 days a week. there’s always more email, more meetings. you’ll sacrifice sleep to get things done, but you have a family, and you’ve spent time with them, too – not just time, but being there, being “present” when it’s not work-time and fully engaging in real life, in things that you like that aren’t related to technology. you know you can’t get that time back. time is your most valuable resource. it’s invaluable, in fact. and, just like any good investment, this approach will pay handsome dividends, as well. while work/life balance may not be
attainable, you must continue to pause and take in life.

the journey will be amazing – enjoy it – and stay uncomfortable

cheers,

mike

my name is michael abbott, and welcome to my blog.

my goal for this blog is simple, two-fold. one, to share my story and evolution as an engineer with others, and to attempt to capture the essence of founding, building, and scaling technical companies so that it may be helpful to one other technical founder out there so that entrepreneurs who are in the same shoes i was in over 10 years ago know what i wish i would have known. through these experiences (some good and some not so good), i am inspired to chart my own path as an investor.

a little about me. i grew up playing sports intensely, team sports (soccer, crew, and rugby) for over a decade, followed by individual sports (triathlons, running, and swimming) for another decade. i didn’t realize it at the time, but each sport pushed me in different ways to be part of a team and focus as an individual. it sounds cliche, but at the same time, it defines me. and, i’ve found it’s just more fun to be part of a killer team. without those collaborative experiences, i may have been a very different type of engineer.

i began my technical entrepreneurial journey over a decade ago. after years of being a code monkey in elementary school (apple ][+ ftw), junior high, high school and college, and after dropping out of a PhD program. a couple of years later i started a company in my house, scraped up money to pay the founding engineers, and was fortunate to work with a team that build a venture-backed company that still exists today , a decade later. that was a success.
i’ve been involved in a company that didn’t pan out, too…that was really hard. we often don’t reflect on the ones that didn’t work out, but they’re important. more recently, i managed to head over to palm and led the team that built/shipped webOS, and most recently, led the engineering team at twitter where it is great to both the service and the team scale to new heights! be gone fail whale!

after twitter, i was fortunate enough to join kleiner perkins at the end of 2011, and this is what i’m going to do for the rest of my career. already just a few months in, and i love it. i love every minute of it. things are changing fast in the valley — and at kleiner, too — and i’m lucky to be a part of it. i have scaled technologies, teams, and companies, and also participated in rebuilding efforts at other times. i’m now trying to scale myself — as strange as that sounds — so that i can help the next generation of great technical entrepreneurs build the next big things.

if you’ve gotten this far, thanks! i’m going to post here about once a month, maybe more, and simply try to capture whatever knowledge i acquired over the last decade in the hopes that it will help others who are on the verge of starting their first, second, or third technology company. specifically, i want to cover all items a technical founder will face — from fundraising, to hiring, to recruiting, to scaling, to when to bring in nontechnical hands, how to pick advisors, and much more. if you have ideas, please also share below. i’m looking forward to it!

-mike abbott
@mabb0tt on twitter