Rebooting Startup Lessons

I set a goal five years ago to blog regularly about my day job running a software company. I setup the Startup Lessons category and managed a handful of posts that year before things stalled. Since then, most of my Startup Lessons have been about related books or riffs on interesting posts.

So after a lengthy hiatus, I’ve decided to reboot Startup Lessons. My (new) goal is to write at least one post a month sharing what I’ve learned running a business over the past 15 years.


So why am I doing this? There are plenty of resources out there covering startups and running a business. There’s a wealth of books, blogs, online and offline resources available. Trust me, I’ve read a lot of them. You can see a sample of what I’ve read in the Startup Lessons archive, which covers books from the last 5-6 years. There are even more books I read before that. It would seem there is little I can add to an already heaping pile of advice.

What I’ve found in my reading is that every book, every resource speaks to me differently. There are some books which I’ve found incredibly helpful, and others, well, not so much, Interesting enough, all the books came highly rated. So it really comes down to which books resonate with you, and which books are most applicable to your situation.

For example, if you’re starting a restaurant, a book about software startups isn’t going to be particularly helpful. Likewise, if you’ve raised millions of dollars, reading a book about bootstrapping a company is not going to be very applicable.

Who will benefit?

You see, not every startup is glamorous and has the fairy tale ending of Google, Facebook, Microsoft, Amazon, or Apple. In fact, most startups and new businesses outright fail, while others turn into solid, profitable ventures that serve a specific niche, or morph into lifestyle businesses that supports the entrepreneur/business owner(s) and a small group of employees.

My intention is to write for people who are just starting out or are mired in what I like to call the grind. I want to prepare people for what’s ahead when they start a business and share what I wish I knew when started my journey. It will be most applicable to those people who intend to bootstrap their company or raise a small amount of money from friends & family or angel investors. If you’re a venture backed startup that has already raised money, intend or need to go the VC route, or work with an incubator or accelerator, I doubt my advice will resonate. I also expect you will have access to lots of other resources and mentors who can guide you down the startup path. Even more specifically, the lessons will be geared toward those starting and running low capital intensive businesses in the software space.

How to read the lessons

As you read the lessons, continually ask yourself why you’re reading and what you want to get out of them. Read analytically. I’m not writing the startup operating manual. You may agree and get good insight from some of my experience. Some lessons may not be applicable. Other lessons you may disagree with, and that’s OK. The point of reading is to engage in critical thinking. Use the knowledge and experience I’m sharing, as well as that of others, and apply it to your situation. Consider what things are applicable and use them. Consider what things are not, and discard them.

Parting thoughts

Keep in mind that the lessons I’m sharing are written from the perspective of someone in the trenches. Even though I raised a small seed round from Friends & Family, that was over 12 years ago. I consider myself more of a bootstrapper at this point and intend to stay that way, at least for the foreseeable future.

My lessons won’t contain ‘the answer’ or ‘the one thing’ that will make you or your business successful. Unfortunately, I’m not selling magic beans. If I had them, I’d be using them myself. I also don’t have, nor will I promise, any solutions that will help you get rich quick. Starting a business is a grind, a slog. It’s hard work. It takes a willingness to jump into the trenches and get dirty. No matter what you read, see, or think, all successful entrepreneurs put in the time and effort it took to reach their level of success.

My assumption is that you are going to read my lessons because you’re thinking about starting a business, you’re struggling figuring out how to start, or you’re caught up in ‘the grind.’ If you’re thinking about or struggling to get started, I hope my lessons will give you the motivation to make the leap. If you’re caught in ‘the grind,’ then I hope these lessons will help you refocus and recognize that you’re not alone and that we’re all in this together.

And at the end of the day, my lessons alone will not make you successful. It’s your ideas, your hard work, and your belief in yourself that will get you through to the other side. I hope to see you there!

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