The Stairstep Approach to Bootstrapping

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Between this blog, my podcastMicroConf and the Micropreneur Academy, I’ve had the privilege of watching hundreds of entrepreneurs launch products over the past decade (even into the thousands, depending on how you count).

After a while, I started to notice a pattern emerging among the pool of bootstrappers who were able to successfully replace their income, buy back their time, and quit their jobs.

I first captured this pattern in my notebook in early 2009, but I didn’t have enough data to be confident in the theory. I started embracing it as a framework on my podcast around 2010, and in 2013 I gave it a name.

I call it The Stairstep Approach. After fully fleshing it out in my talks at DCBKK and MicroConf Europe last fall, I’ve been struck repeatedly by how many successful bootstrappers have followed, or are currently following, this trajectory.

The interesting part is that my own path moving from consulting to products followed the same steps, as you can see in my product revenue chart from the past decade:

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How I Created 4 Startup Explainer Videos for $11

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When I was writing the copy for the home page of Drip, I ran into a bit of a challenge: the idea of marketing automation is still new to a lot of people, so not everyone is aware of how email marketing (much less marketing automation) can help them.

One of the easiest ways I’ve found to explain the value of Drip has been making screencasts, walking people through the product and pointing our very specifically how Drip can help in their particular use case.

But making a personalized screencasts for every trial customer isn’t realistic, so I put my mind to finding a way to make this a little more scalable. After discussing with Derrick we came up with the idea of creating a few explainer videos to walk visitors through how I would tag, segment, and structure a Drip account for a few different business types. 

Normally, I prefer to use contractors (typically those who offer productized services) for basic marketing elements so I can focus on higher-level tasks, but in this situation there was a catch…

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My New Podcast Launched Yesterday, It’s Called “Zen Founder”

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My new podcast launched yesterday. It’s called Zen Founder, and it’s focused on finding the balance between startups, relationships, and life.

I co-host it with my wife Sherry, a clinical psychologist, and the first 4 episodes are ripe with discussion about:

  • How to stay sane while starting up
  • How to structure an annual retreat
  • How to punch procrastination in the face
  • How to deal with depression and setbacks

Listen on the web here

Or subscribe in iTunes here

If you use a podcatcher such as Downcast or Stitcher, it should be available by searching for “Zen Founder.”

Give it a listen and let me know what you think. If you enjoy it, would be a huge help if you’d give it a shout on Twitter.

Launch: The 2-Hour Audio Documentary of a Startup

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I’ve just released a 2-hour audio documentary chronicling the story of building and launching my latest startup, Drip.

Launch. A Startup Documentary was compiled and edited from 9 months of Skype calls between myself and my software developer, with an epilogue recorded 1-year later (about 2 weeks ago).

From the honeymoon period of “green field” development to the sleepless nights of database failures, Launch captures the real-life angst of building a startup.

The goal of this documentary is to fight the press-portrayed startup myth by pulling back the curtain as a company is being built. There is no champagne-popping, no hockey stick growth, and no overnight success.

Only a couple years of hard work and uncertainty documented  for your listening pleasure.

Listen in your browser or iTunes.

 

SketchNotes of My 2014 DCBKK Talk: “Optimizing Lifetime Value: How to Make More Money from Your Business”

In October I spoke at Dan & Ian’s DCBKK event in Bangkok, Thailand about how to make more money from your business.

Through the mad illustration skills of one Maggie Appleton, here are SketchNotes summarizing my entire talk in a single image (click the image for a hi-res version).

SketchNotes of Rob Walling's Talk at DCBKK 2014

The Biggest Gamble of Your Career

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I’m in the midst of the biggest gamble of my career. The thing is, every chance you take feels like your biggest gamble while you’re taking it.

When I left salaried employment for consulting in 2006 it felt like a big gamble.

When I left consulting for product in 2008 with a wife, kid and a mortgage, it felt like a huge gamble.

When I spent most of the money I had in the bank on a broken-down SaaS app few people had heard of, called HitTail, I was downright scared. It’s hard to put years of work and savings on the line, based on nothing more than confidence that you will execute.

Upside
But every one of the above gambles worked out, and I wound up far better off than if I’d never taken them.

And here’s the thing…

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Buy Yourself Time by Systematizing Your SaaS With Trello

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This is a guest post by Kyle Brown, author of the upcoming book Systematize.

Are you spending a lot of time explaining how to perform tasks to your employee(s)?

Do you have documents scattered all over the cloud, various emails, and computers?

Do you struggle to find documentation when you need it?

If you answered yes to any or all of these questions, then hope is not lost and there is something that you can do.

You’re running a SaaS business and likely don’t have the resources or the desire to hire an individual or management company to run the operations of your business and you cannot be everywhere all of the time. Spending your time repeating endless cycles of q and a are not the answer to growing your business.

Image if you had more time to market your business or work on a new feature for your SaaS to increase the profits? What if you could consolidate all of your methods for performing tasks into a clean organized manner so that you could easily find and share information required to run your company?

In this post I outline how you can take your mind share and knowledge required to perform tasks in your business and document them so that your team can execute in your place. The method is also known as systematizing. Also referred to as standard operating procedures and business process management.

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Building a SaaS Business You Can Sell

This is a guest post by Thomas Smale from FE International, a website brokerage with an emphasis on SaaS apps.

At FE International we speak to website owners on a daily basis who are looking to sell their businesses. Unfortunately, many of these businesses are not sellable for a number of very avoidable reasons. Planning your exit in advance (even if you have no intention of selling now) is always the sensible thing to do and will put you in good stead, saving you headaches when you do decide it’s time to move on.

SaaS products have always proven to be very popular with buyers over the years. Last year we sold 78 web-based businesses, so reflecting on these we’ve pooled together our collective experience to show you what really improves the saleability and the value of a SaaS business in the eyes of a new potential buyer. A combination of these factors could be the difference between selling for 1x EBITDA (if done badly) and 3x (if you follow these rules).

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Reaching Escape Velocity as a Bootstrapper

Escape Velocity

This article was a guest post by Bronson Taylor who is the host and co-founder of Growth Hacker TV, where the experts on startup growth reveal their secrets.

Escape velocity, in physics, is basically the speed needed to break free from gravity. The idea of escape velocity also surfaces in regard to startups; David Cummings says that, “For startups, escape velocity has to do with becoming the dominant vendor and growing indefinitely.”

I agree with David, if we are referring to VC backed startups, but bootstrappers have a very different notion of escape velocity. After almost 100 interviews on Growth Hacker TV, I have come to realize that a self-funded startup is not trying to reach a 10x return on a multi-million dollar investment.

Escape velocity for a bootstrapper might be freedom from the monthly bills, or freedom from a full-time job outside of their startup. Bootstrappers don’t need to escape from competition and become the “dominant vendor.” They require much less velocity because they are escaping a different kind of gravity.

This is an extremely important distinction because most of the growth advice online makes the assumption that everyone has venture capital. However, if you are self-funding your startup, here are four rules for reaching escape velocity as a bootstrapper:

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Growth Hacking Without Venture Capital

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This article is a guest post from Bronson Taylor. Bronson is a co-founder and host of Growth Hacker TV, the only educational platform focused exclusively on helping startups grow by acquiring, retaining, and monetizing users. They have over 60 episodes, with guests from Twitter, Facebook, LinkedIn, DropBox, and many more. Image above from Toban Black.

Founders sometimes assume that they need an influx of cash to truly grow a product. Luckily, this isn’t true. The confusion arises because we fail to make a distinction between the growth strategies that are relevant to venture backed startups as opposed to the strategies that are relevant to bootstrapped startups. These strategies overlap, but the differences are immense.

You can grow without money, but only if you stop imitating the startups that have closed a round of financing. As the host of Growth Hacker TV I have become keenly aware of these two parallel worlds, and this article is my attempt to outline the primary ways to think about growth when you are building a product without investment capital. There are plenty of blog posts for the funded so let’s even the score a bit.

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