Post Category → Best Of

How I email

In 2019 I’m transitioning into the role of an investor at Earnest Capital. Since we soft-launched in October with a call to collaboratively build investment terms for “funding for bootstrappers” I have received 100x the normal volume of emails that I’m used to processing. Looking forward it seems clear that being an investor in early-stage startups means becoming a professional emailer. As I’ll be spending most of my day in email1, I thought it would be a good idea to explicitly state my email preferences somewhere I can link to.

This should simply be viewed as a list of my preferences, not some list of demands that must be complied with in order to email me2.

Things I think about email

  1. Many VCs seem to view responsiveness as a competitive advantage, replying near-instantly at all hours. I’m not sure that’s a factor I want to optimize for but even if it were, I know I would never be an exceptionally fast responder. So I’m not going to compete on responsiveness. If you’re used to dealing with VCs and getting instant responses, emailing Earnest might seem jarringly slow but I’m okay with that.
  2. I optimize for completeness in a response. I prefer not to trade 25 half-baked emails back and forth when I could wait for all the facts I need and write a detailed, clear, complete response.
  3. I am remote-first and I prefer emails as the default mode of communication. Switching to scheduling a call the moment an issue becomes complex is a habit I don’t share. Let’s be thoughtful, clarify our thoughts in writing, and use a call as a last resort (or just something that’s fun but not necessary).
  4. I don’t do Inbox Zero. I used to, but feel that I frequently need more time for responses to marinate than an instant ‘respond, delay, delegate’ protocol allows.
  5. I do view my inbox as “other peoples’ todo list” and try to allocate my day first toward larger projects that will improve Earnest for everybody, then dive into my inbox.

My email preferences

  • I like long emails. I’m not one of those people who needs to get all the information in the first 3 sentences or I stop reading.
  • Follow-up as much as necessary. If I haven’t responded to your email, it doesn’t mean I won’t. I am most likely working on something else integral to a reply. Feel free to send additional follow-ups if there is new information. I prefer not to get a daily stream of “just bumping this to the top of your inbox”—though one or two is fine.
  • Please let me know explicitly if my default mode is not going to be appropriate. “I really need an answer on this by {datetime} because {reason}” is really helpful for me.
  • Don’t apologize. If we agree that sending me an email does not obligate me to send back an immediate response, there’s no need to apologize ✌️

Myers Briggs for Email?

We all spend so much of our lives writing and reading emails. Many people have radically different styles and preferences. I wish more people would explicitly write out their email preferences. Eventually, we’ll categorize and group them into themes like a Myers Briggs for email. So just as you can short-hand with “I’m an INTJ” and confer a lot of information on how you prefer to interact, you can say “I prefer my email as Correspondence” or “I’m an aggressive Inbox Zero-er” and confer a lot of the preferences above. I view my email preferences as Correspondence in reference to how people used to communicate when hand-delivered letters might take months to be delivered by ship. You had to be thoughtful and clear and close as many open loops as possible.

  1. I’m using Superhuman these days as I write this.↩

  2.  hat tip to @devonzuegel for the inspiration for this↩

Selling My Bootstrapped SaaS Business

Five years ago I built and launched the first version of a SaaS app on a single flight from San Francisco to Buenos Aires. Slowly and steadily, Storemapper grew into a healthy location-independent business for one person and then later a small dedicated remote team. At parties, I would describe it as, “not a startup; a healthy growing internet small business.” This year, almost exactly five years after launching, I sold the business for what, to someone growing up middle class in Florida, is a life-changing amount of money that will enable all kinds of exciting new projects and adventures. From start to finish, it has been an exciting ride, much of which I have documented here on the blog. With the sale concluded, I wanted to share as much as I could about the process of building a business that can be sold and how I sold it.

There’s always a risk that these posts turn into a 5,000-word humblebrag. But I really do think it’s worth a read because, unlike most business acquisition stories, which often feel like an out of the blue stroke of good luck, the way that I sold Storemapper feels very replicable for other entrepreneurs. When I spoke to someone two years ago about what it would look like if I ever sold the business I would say, “I’m not trying to sell it now, but if I ever did it would probably look this…” And six months ago I would tell a few folks privately, “I think that one of the people I met recently might be the one to buy Storemapper and if they do it will probably go like this…” And, then basically when it all went down it looked more or less like… that. There wasn’t some single huge stroke of good luck, though of course, I got lucky in the little ways that every successful business has to. An excellent outcome, but also a perfectly reasonable and achievable one that I think can serve as something of a template for other bootstrapped entrepreneurs.

This is a long and detailed post. I had so many questions going into this process and I didn’t find a ton of good posts from the founders perspective on selling bootstrapped businesses. So I thought I would just throw everything I could think of into a post and let you skip around or save it for reference when you’re considering selling your own business. Grab a pot of coffee and let’s get started.

First the obvious: why sell your software business?

Continue reading →

How to Get Startup Ideas: The Meat Grinder Approach

There are a million books and blog posts on how to get startup and business ideas. Many people think the biggest road block to successful entrepreneurial life is having that one great idea. Once you get even a modicum of success, lots of people will start asking you about how you got an idea like that, and for any tips and tricks on how to “come up” with a similar idea.

The concept is extremely tantalizing and sounds so imminently teachable that it’s a favorite tool of lifestyle business spammers everywhere. 7 Step Guide to Profitable Business Ideas. Join My Webinar on Finding Your Dream Business Plan.

But this is entirely the wrong way to think about it.

First of all you should be coming up with at least five possible business ideas every day. This part should be basically effortless. People trying to sell this part are scamming you.

If you are going to be a successful entrepreneur at all you should innately be looking around you at your life and the lives of others, thinking what are their problems. What are their desires. What do they spend money on. Which of those things are broken or could be done massively better or cheaper or faster. You should be constantly thinking this way. It should annoy people who spend a lot of time around you.

If you’re not doing that, you’re probably not going to be an entrepreneur… sorry. It’s okay. There are lots of other great life paths but this one isn’t for you.

There is one common exception to the rule. You might be hung up on one idea, and that stops the process of thinking of new ideas. It’s cool, you just need to build yourself a better meat grinder.

The secret to coming up with a successful business idea is putting hundreds of ideas through the meat grinder.

Continue reading →

Debt Free

I turned 30 last week and as a birthday present to myself I paid off the last chunk of the nearly $60,000 in debt I accumulated trying to build a software startup. I thought I would write a little about what that’s like and whether I’d do it again.

In the Summer of 2011 — four and a half years ago… dang — I quit my job.

Continue reading →