[6] 10 First-Year Mistakes & Lessons Learned Bootstrapping a Startup – [Free Report]

As you may know, I’ve been bootstrapping various startups for a several years now. I managed to build them to a point that allowed me to transition out of consulting to focus solely on products.

But the path to get here certainly wasn’t smooth sailing. I made mistakes. Lots of mistakes, actually. In fact I’m still making mistakes today. The key is to never make the same mistake twice.

And that, my friends, is what led me to create this report.

It contains the stories of ten big mistakes I made during the first year my startups, and the lessons I took away from them.  My hope is this will help you avoid some of the same pitfalls and get to where you want to be a little faster.

I have included the first 3 (of 10) mistakes & lessons below.  If you’d like to read all ten, sign up for my newsletter below and I’ll send you the full report (PDF).

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Before we dive into those first 3 mistakes, let me step back a little bit, and tell you about the real motivation behind this report:

Sure I hope these lessons that I learned the hard way while bootstrapping my startups will help you avoid some of the same pitfalls.

But more importantly, I hope you will give some serious thought about the path that you’re currently on.

What are the mistakes that you’re making right now?

And if your answer is you’re not making any mistakes, well, that right there is a mistake in itself.  You should be mistakes.  Because that’s what learning by doing is all about:  Making mistakes, then soaking in a valuable lesson.

So I hope that more than anything, this report will help you or inspire you to take a hard look at your business.  Look back on the previous months and years, and pinpoint a few things you could have done differently.

  • Why did you choose these things?
  • Specifically what did you do wrong?
  • How will you correct them next time around?  

I believe in being critical of yourself and having an open mind about that.  That’s the best way to get better and step up your game.

Now here are 3 of the mistakes that I came up with as I took a hard look back at my own business…


MISTAKE #1:
I invested my own money in the wrong places

As I started building my SaaS business, I knew the majority of the investment would be in the form of my own time (or overtime, if you will). But I also set aside $5,000 of my own cash to invest into getting the business off the ground.

That $5,000 quickly grew closer to $8,000, and that was before I had any paying customers! But my mistake wasn’t the amount of personal cash investment I made. It was how I allocated those funds.

I failed to recognize which things I was really good at, and which things I was mediocre (read: a “hack”).

If you ask me which skill comes most naturally to me, it would be design. Yet, I chose to hire designers to mockup the first version of my site and my logo. Meanwhile, I spent most of my time tangled in code. I can code enough to get by, But I don’t do it particularly well, and certainly not very fast. In other words, I could spend a week figuring out how to code something that a seasoned developer can whip up in just an hour.

I failed to distinguish between a mere ability (coding) and my true strength (design).

On top of that, the designer in me ended up re-doing all of the design work I that I had spent my $8,000 on!

Looking back, that cash would have been much better spent on accellerating the development work, while I focused my time doing the design work. I also would have liked to set aside more cash to put towards early (paid) marketing campaigns, but since I burned through it so quickly in the beginning, that wasn’t an option.

Lesson learned: Distinguish between your mere abilities and your true stengths. Allocate your resources accordingly. (tweet this)

MISTAKE #2:
I tackled too many tasks at once

During the first year of my products business, I made the mistake of loading up my plate with any and all tasks that flew my way. I would jump from task to task haphazardly with no consideration of setting an order of priorities.

When a customer emails with an “urgent” request, I got right on it. When I came up with a “really cool” idea for a new feature, I dropped everything to start building it. When I listened to an inspiring course on Mixergy, I’d completely change my whole marketing strategy on a whim.

I was doing a lot of things and staying very busy. But I wasn’t making clear progress towards a defined goal. It felt like I was running in place.

I finally realized this mistake and built a system around how I choose which things to tackle and when. I make a point on the 1st of every month to list out the 3 or 4 “big things” I plan to accomplish in the next 30 days, then I set my weekly and daily to-do lists according to that plan. I even started making 6-month plans, listing out even bigger things I plan to accomplish in the next half year.

Lesson learned: Plan your tasks for the next month and six months so that you can prioritize Today accordingly. (tweet this)

MISTAKE #3:
I didn’t seek outside advice

As a bootstrapper, I’m very much of the “do-it-yourself” mindset. Or better put, the “figure-it-out-myself” mindset.

But that can only get you so far, and in fact, can often lead you down the wrong path. Sure, there are lots of resources available online, such as blogs, courses, ebooks, and so on, which provide a healthy dose of education. You can also learn a lot from getting your hands dirty and tackling things yourself (or as I call it, “Learning by Doing”).

But there is one more resource, which is even more valuable than all of those: Learning from the experience of others.

After a year of trying to do (and learn) everything all by myself, I finally started making a point to personally reaching out to folks who are doing similar things to what I’m doing and asking to pick their brains. I would ask specific questions and find out what they learned from trying things out.

I also joined a weekly mastermind group with 5 other online SaaS business owners, where we support and advise eachother about our challenges in our business.

Building a support network of talented, experienced, smart, and helpful entreneurs has helped me work through some difficult challenges and helped me find clarify much quicker than when I tried to work through them all by myself.

Lesson learned: It’s never too early to start building your support network, especially when you’re a solo bootstrapper. (tweet this)

Read all ten mistakes and lessons learned by entering your email below:

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  • Mark Pierce

    Nice article! I tackled too many tasks at once like to you listed in mistake #2. I can at least say I have allocated specific tasks and time spent on these tasks
    per day. I also enjoyed what you said, if you are not making mistakes we are not growing and learning from our mistakes.

  • Ms.Phoebe

    Great article! So many people don’t talk about their pain points, it is nice to see you do it so honestly. You’d be surprised how many people who have been down this road before. Seek them out, listen to them, ask them questions and learn from them. Here is a great article similar to yours about the company Matchist.com and the lessons they learned in their first year: http://goo.gl/uDvBcJ

    • Thanks! On my reading list.

  • Myson Jones

    Hey Brian,

    I’m 3 years late to the partner, but I figure this is evergreen content. Is this report still available?