Transitioning from Maker to Manager

Ira Glass, the creator of the radio program This American Life, has this famous quote that’s worth reading in its entirety:

“Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know its normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take awhile. You’ve just gotta fight your way through.”

It’s such a useful insight for creative work. It’s also a broader lesson that the thing that will be your ultimate strength can be, during a transition phase, a weakness that you have to overcome. Having great taste is ultimately something that will make your work great, but in the short-term, when you are beginning to learn a craft, that same taste tells you that your work is worthless. Your taste makes it hard to persevere through the practice and master the craft to a level a worthy of your own taste. To make it through that phase, you have to let some bad work happen—your own—and have faith that the process will improve it over time.

Something similar happens often when making the transition from a maker to a manager. Credit to Paul Graham for pointing out some important differences between makers and managers in the modern workplace. Although in this instance I’m not talking about scheduling, but taste or something like it.

Most of the people I know who are now managers, didn’t go to business school and train to be a manager, they started as makers. They started as founders, doing all the making at a company they created from nothing, or they started as key individual contributors, the first marketer/designer/developer at a small organization. Over time the organization grows, to hit its goals it needs a design team and an engineering team, and so talented individual contributors start hiring, resourcing, planning and managing.

And here is the most important skill I know for making this transition smoothly and effectively:

Let bad work happen.

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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?

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Build Your Own Personal Robot Army: Part 1

I never set out to build a robot army. But today, there are at least a dozen little robots who do my bidding on a daily basis. Between managing my personal life and running my Micro-SaaS Business (Storemapper), my robot army does drudgery while I sleep and makes my life a little easier and more productive. Here’s how you can build one yourself. In Part 1 I’m just going to look at the robots that required no coding to set up, later I’ll do a post about all the little custom scripts I’ve got running on Heroku Scheduler.

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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.

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Technical skills for non-technical people in tech

Tech is one of the few growing bright spots in the job market and understandably a lot of folks want to figure out how to get a job at tech startups.

When I quit my job and started getting into tech/software/startup things I was “not technical” — meaning specifically that I didn’t know how to write software. I’ve had lot of conversations with people trying to break into the market who are also not technical, didn’t grow up hacking, didn’t get a computer science degree and can’t write a line of code. I taught myself to code so a lot of the conversations start there: “Should I learn to code?” While I was technically non-technical in startup parlance, I am in fact a pretty technical person and spent a good part of my pre-startup career mastering nerdy things like Excel Macros so it made sense that I would eventually learn to write my own software. But for many people I’ve talked to, I don’t think learning to code, to the point where they would actually be able to get a job as a software engineer is a good idea.

So how do you get into tech if you’ve decided that you don’t want to write code.

Many people respond by really emphasizing things they believe to be the antithesis of technical skills: salesmanship, networking, being a people person. Maybe it was once the case that all software engineers were antisocial nerds incapable of expressing themselves in public who were dependent on non-technical people to get things done, but that is not at all the case now. Startups increasingly brag about their focus entirely on products, their salesforce of zero, their T-shaped team fully capable of writing and speaking convincingly among everything else.

It’s true, if you are good at sales you will always be able to get a job, but if you are young, or without a ton of relevant experience, and trying to get into tech, there are just too many applicants claiming to be able run through walls and sell snow to eskimos.

Learning to write server code and deploy apps is not a good fit for everyone at a startup, but there are quite a few non-coding but still a bit technical skills that I would highly recommend acquiring. Every startup will value this skill set and in many cases developer/designer colleagues will love you for having them.

So this is my proposed list of technical things non-technical people who want to get into tech should learn.

Know how to use a task managers correctly

Create some test projects and learn how to use Asana, Trello or Basecamp or all three. Learn all the features. Read the companies blog posts and tutorials. Because they are so product and engineer heavy, tech startups tend to live and die by their task/project management apps. Nothing is more annoying than adding someone to the team who keeps adding tasks as subtasks, not tagging correctly, forgetting to add due dates and so on.

Onboarding someone who seamlessly jumps into the project, and even starts cleaning up the task manager and making others lives easier is a dream come true for startups trying to grow the team rapidly.

Email marketing and marketing automation

For all the times journalists have proclaimed the death of email to be nigh, sending email is still an essential activity for all startups. Despite evidence that building an email list and talking to it regularly is very profitable activity, most startups actually don’t send enough email to their customers and prospects.

This is mainly because email marketing systems are still not that easy to use. Brilliant copy can get completely mangled by a poorly edited email template. Forget to check a certain box and your email is completely unreadable on mobile devices. Did you insert the FNAME variable correctly or did you send 12,000 emails addressed to “Dear insert name,”

Make a newsletter of your family and friends and practice sending emails, playing with templates, add call to action buttons and learn how the analytics dashboard works, how to track opens, read and click throughs.

Learn some basic email marketing automation such as how to build a welcome/onboarding course the sends new users an email each day after they sign up.

Mailchimp, Aweber, Drip are a few good options to try out.

Become a form wizard wizard

Forms are still the most underestimated web tool and with form wizards like Wufoo, Google Forms and Typeforms, they can be deployed in powerful ways without any coding at all.

It’s amazing how powerful a good form linked up to email marketing can be. Learn all the different field options. What other apps can be integrated. Should you build a Google Form and output the data directly into a Google Spreadsheet, or a Wufoo form that automatically enrolls signups in an email course on Mailchimp?

Do you really need an engineer to deploy a payment processing system when you can accept payments directly in Typeform without writing a line of code?

CSS tweaks

CSS is not coding and basic CSS is very very easy. It’s just a matter of learning a simple, declarative vocabulary. There are no complex functions, no math, and basically no variables. You can want to turn the text on your embedded form the same dark gray as your company’s landing page text you just need to learn how to say that in CSS:

#my-form label {color: #333}

Take a Codeacademy course and watch a bunch of videos on CSS Tricks.

Learn the most common Content Management Systems

Every startup has landing pages and almost every startup has a blog. Most of these are run on WordPress or Squarespace. Learn how to add and edit a simple page in each of these, learn the default options and how to add your forms and email signups widgets to each of them.

Being the idea person is one thing, but being the person who can create ideas, put them on a landing page and A/B test pricing options is a 10x more valuable.

A little knowledge of forms, email automation, CSS, and how to create a page in a CMS and you can execute that without writing a line of code.

Internet superpowers: Zapier and IFTTT

Here’s where you can out-tech the tech people on your team. When faced with basically any problem: Coders gonna code. This frequently leads to unnecessary custom-built solutions for fairly simple automation.

Two services: Zapier and IFTTT let you automate interaction between hundreds of apps and services without writing a line of code. Do you really need a fancy dashboard to run a cohort analysis of you email signups or can you just have Zapier export every signup into a spreadsheet and run a few Excel functions on it? Taking that off your engineering team’s plate so they can focus on the core product is a huge win.

Learn how to automatically create a support ticket for everybody that tweets at your company, send your inbound leads directly to your task manager so they all get assigned properly and followed up with quickly.

Bring your own army of outsourcers

Your startup’s lead designer is spending the afternoon redesigning the app onboarding process but you really need someone to remove the whitespace from a few logos so you can get a press release out the door. Interrupting their flow for such a little task is a huge drain, instead you should get very very good at using oDesk, Elance and Fiverr to outsource little jobs like that. You can often find freelancers to do things for incredibly low cost (e.g. $5) such that even if you were paying for it yourself it would still be worth it. But there is some overhead of time that you have spend familiarizing yourself with the process, learning how to select candidates and learning the hiring/managing workflow for each one.

Start spending some time and little money now developing that skill. The best part is you can save those freelancers in your account to call on later, an incredibly useful resource for you and your company.

Conclusion

Even if you had literally no other valuable skills, proficiency in all of these categories would be enough to get a job at a tech startup. You’d probably have to call yourself a growth-hacker or technical-marketer but you would definitely be valuable to almost any startup.

The last question is how to express this skillset to potential employers. The answer is LINKS. You must send links to THINGS. Startups do not care where you went to school, what your GPA was, who wrote you letters of reference. They care about what you made. So build a personal website, hire a freelancer to spruce it up, manage that freelancer in Basecamp, write about the process of hiring and managing that freelancer. Start a newsletter for a cause you care about, build a cool form for it on their site and learn from the analytics. Write a case study about that and put it on your site. Then send links to all of those things somewhere very early on in your job application.

Good luck.