When Entrepreneurs Wander: Lessons Learned Dicking Around

Posted by Neha Palacherla /October 22, 2013 / Entrepreneurial Advice, FounderTalk

This guest post was written by Dan Grover. Previously, he founded the music software startup Etude. He has also built products for Nike and Udacity. Currently, he’s working with partners iterating on concepts for his next venture at Brown Bag Labs.

When I was asked to contribute to the “FounderTalk” series on this blog, I thought I’d talk about my first startup, Etude. It was an early iPad app for downloading sheet music for songs and learning how to play them in an interactive way. I sold the company to Steinway & Sons in 2010, where I led a music technology team.

I started to recount that experience — about how I moved to Palo Alto, lived in a “hacker house”, grew the business, nearly got sued, got acquired, moved to New York — then realized that each re-telling of the story grates at me more and more. It’s because the events happened three years ago and all I’ve done since are few stillborn attempts at a next big project, some traveling, some consulting, a couple jobs. Altogether, the time I’ve spent wandering adds up to be more than the time I spent on the one small, phyric success I’ve had.

So I decided to write about that instead. Wandering is important and deserves as much coverage as all the war stories and “hero’s journey” type material we hear so often. But I’ve begun to suspect that there’s a right and a wrong way to go about it. It can be a stepping stone to better things or a time-wasting detour. How do you know? Here’s what I think is worth considering:


If you’ve been devoting every waking hour to your startup, you might think a lot about the difference in work/life balance you’ll experience by working at someone else’s company.

If you’re worn out, the idea of being able to “go home” and be able to spend your now-copious free time on hobbies, on side-projects, and with your significant other is alluring. But from my experiences with both, it seems like, regardless of how we allocate our time, we have a finite amount of “brain real estate.” When you take a job, you’re really renting out a chunk of your brain. It’s still being rented even when you’re not on the job (in the same way that you’re still paying for your apartment even when you’re not in it).

A couple times of I’ve taken a full-time job that seemed interesting to me with the idea of “coasting for a while and getting time to think” only to find myself obsessed with my duties at the job every waking moment. And I can’t say there haven’t been weeks while working on a startup where I’ve slacked. Your mileage may vary, but I’ve come to the conclusion that work/life balance is not something an employer can bestow upon you. It’s an attitude choice to make every day. I’ve begun to think there’s some credence to 37signals’ claim of “40 hours is plenty.”


The most straightforward reason to take a job is because you’re feeling poor. If you have debt or you’re in actual danger of privation, I won’t try to dissuade you. But I’ve been surprised, when talking candidly with friends, about where their personal barometer for this is. It’s often far lower or far higher than my own. It’s worth thinking hard about it and seeing if it really makes sense.

When I fell into my first software business (the one that would become the startup), I had little understanding of just how different finance in companies is from personal finance. I’d compare the business’s cashflow to my own at various hypothetical jobs, which is more apples-and-oranges than I realized at the time. If you haven’t already, I’d highly recommend taking one of the free online courses on financial accounting or startup finance so that you have a better mental framework to view the money aspect against. I lived with an incomplete understanding for years and it definitely harmed me.


Another difference you’ll find yourself pondering is which skills you’ll be applying and building in the job versus what you’re doing now. The duties you accept in a job have real power to shape the type of person you become. Always remember that people want to hire you for a role that’s going to be good for them at the time, not necessarily good for you.

If you join a company (particularly if you’re going to be just an engineer and not even a PM), you may be divorced from the rest of the process in an uncomfortable way. Companies have silos. They have meetings. It feels inefficient and finicky and can make you crazy.

The insight I had after working at a couple big companies was that the inefficiencies I saw at the ground level weren’t a big deal. It didn’t matter that it took five people to do what, in a startup, could be one person’s job. I realized that the “many hats” mode of working I had fallen into while starting up could be startlingly inefficient. There was a switching cost that I had been making up for by working longer hours. This became especially apparent to me after the acquisition when I had the chance to hire help, as well as in a product-management role I later took. I became the bottleneck in many situations. I didn’t delegate as much as I could because, in my mind, there simply was no separating the idea for something from its design to its implementation.

I’ve learned, through some pain, to change that. I spend more time wireframing, prototyping without code, and getting input from people before building something. It used to seem like a dumb thing to do if you actually were capable of building something fast, but it actually is much better that way.


There’s a memorable bit in the opening to The Scarlet Letter that claims that the first allotments of land the Puritans made in every new town were for 1) the cemetery and 2) the prison, regardless of how utopian they envisioned their future settlement to be.

For modern pioneers in the digital realm, the first two things brought to every funded startup’s office, after the lease is signed, are 1) a massive shipping palette containing every snack food carried by Costco, 2) a foosball table, 3) a high-end espresso machine. Later on they worry about pesky things like business models.

Startup offices these days just seem so gosh darned happy, especially if your day-to-day is hacking out of a cramped studio or coffee shop. It seems like a dumb point to address — to suggest that such a frivolous thing would affect our decision-making — and yet companies spend money on it because it always does. If you’ve been working out of coffee-shops and apartments and it’s bumming you out, just find a way to pony up for office space.


You may be taken in by the success a company has had in its field, or the amazing press it’s received. “Surely,” you might think in one of your more dour moods, “I’d rather have a chunk of that than the pissant thing I’m working on now.”

I’ve always been charmed by the stories of early Apple employees on Folklore.org, or Jamie Zawinski’s accounts of Netscape, or even Feynman at Los Alamos. These people were all in the right place at the right time. There was something remarkable and historic happening, and they got to be close to it. I’ve always wanted to find my own version of that somewhere. But the only reason those stories are so romantic is because Netscape, Apple, and the Manhattan Project succeeded in their ambitions. Plenty of other undertakings don’t.

It’s sort of like that scene in that excorable movie The Campaign, where the grassroots campaign Zach Galifianakis’ character is running suddenly gets major funding and the DC politicos swoop in. For many startups, once they raise their series A, the VCs start recommending people. After hiring an office manager, an HR person, and a PR firm, the founders get flooded with emails from someone who knows a guy that knows a guy who would be great for some ancillary role or another. And before the company’s vision has even had time to mature, they’ve got 20 people working for them. Soon enough, they’re moving to a new office five miles down El Camino that’s big enough to fit all the people, the foosball tables, the espresso machine, and the four-ton bag of Kirkland Signature brand trail mix.

If the company’s in a rush to get you on board, know for sure whether you’re going to be another warm body or if there’s actually something you’re pre-eminently qualified to do there. If you’re going to be expected to be a team player, are you really going to be part of “the team”, or are you going to be an accessory to “the team”? Ignore what they say — the equity they offer will speak volumes.


If the financial impact, the lifestyle, the peers, and the role all make sense, you’re still left with the hardest piece of the decision.

Steven Pressfield’s book The War of Art is full of advice for artists on facing resistance and overcoming creative battles. His central piece of advice is to always be asking the question “What is this thing about?” and developing an increasingly pointed answer throughout the course of the project. That, he says, makes facing tough decisions easier. For a novelist or playwright, that question should strike at the essential theme of the work, which helps them edit out parts of the story.

It’s good to be constantly developing an answer to this while building a company. You could frame the question a few different ways. You could frame it as “what is this company about?”, or “who is this product for?” or even, “why am I doing this?”, or “what is worth doing at all?” Write it down in a text file, come up with some answers, and open it again every week to try to chisel more. Try to refine your answer until it is as broadly-applicable as possible.

If you can evaluate the job against the same criteria you have for everything else in your life, you’ll be more likely to make the right call.  In the long term, you’ll end up in a situation that is a heightening of your efforts and not a detour you’ll come to regret— in the greater spiritual sense, if not a financial one.


If this is helpful for you, or you have any crazy stories about jobs that have worked out differently than you thought, I’d love to hear them! Drop me a line on Twitter at @dangrover