Even though my primary purpose for creating Web Masters is to share helpful insights about entrepreneurship from some of the world’s most successful entrepreneurs, it’s also a bit of a selfish project. In its own weird way, it’s an excuse for me to talk with a bunch of incredible entrepreneurs and ask some questions I personally want answers to.
One of those questions is a simple question with a really difficult answer: Why are you an entrepreneur? I ask it because I like to know what motivates people. To be fair, it’s an interesting question to ask of just about any entrepreneur, but it’s a particularly interesting question to ask an entrepreneur who’s built multiple successful companies and is still doing it. After all, those are the people who A) know exactly how much work building companies is; and B) shouldn’t have as much motivation to keep doing it since they’ve already succeeded. So why the heck are they still tormenting themselves?
I bring all this up because I asked one of those successful entrepreneurs — Scott Heiferman — and got a really interesting answer, and decided to share it in this issue’s featured article.
And while I’m on the topic of successful entrepreneurs, this week I spoke with a different entrepreneur for Web Masters — Matt Shobe — founder of FeedBurner. If you’re someone who, like me, pines for the days of RSS, you’ll enjoy hearing from him. (Don’t worry… you’ll also enjoy hearing form him even if you don’t know what RSS.)
-Aaron
How the Founder of Meetup Helped Me Learn to Appreciate the Real Purpose of Entrepreneurship
People become entrepreneurs for all sorts of different reasons. Lots of those reasons —including my own — probably aren’t so great. (But that doesn’t mean your reasons can’t change!)
The Designer Who Helped People Monetize RSS
The invention of RSS feeds was great for Internet users, but it was bad for publishers because people could view their content without visiting their websites. FeedBurner helped fix that by creating an ad network for RSS feeds. On the new episode of Web Masters, FeedBurner co-founder Matt Shobe shares the story.
Check it out on:
…or search “Web Masters” wherever you listen to your favorite podcasts.
FROM THE ARCHIVES…
Everything You Need to Know About Startup Networking Events You Can Learn from Watching the Bachelor
I was trying to leverage some pop culture when I wrote this article. Sure, the Bachelor franchise isn’t as popular as it was back when I wrote this (according to me students… I swear!), the entrepreneurial lesson is still relevant.
Office Hours Q&A
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QUESTION:
Hi Aaron,
I am the owner/operator of a small consulting firm that primarily works with local businesses. It is basically just me, and occasionally I outsource some work to other people when there’s too much on my plate.
It’s at the point where I’ve got consistently more business than I can realistically handle on my own, so I’m wondering how to take the next step in terms of scaling and growing a team.
I guess my question is at what point should one go from a single owner/operator, or basically just working for themselves, to actually running a “real company” so to speak? I’m nervous that I’ll get it wrong when I try to scale and end up costing myself a lot of money when I’m perfectly happy with the life and setup I currently have.
Thank you for your thoughts and wisdom,
Skylar
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First of all, congratulations on your success. Having enough business that you’re even considering hiring more people is a great accomplishment.
As for whether or not you should expand… well… that’s a personal question based largely on your own goals and aspirations.
You’ve indirectly alluded to the argument against expanding, which is that you probably feel like you’ve got a good thing going. You work for yourself, and you’re likely enjoying the freedom of coming and going as you please. Yes, the work is hard, and, yes, clients can be frustrating. But, in general, the experience of controlling your days and daily decision making surely feels liberating (especially if you previously worked in more of a corporate environment).
The argument for expanding is that, right now, you’re in an extremely precarious position. The freedom is great, but it has a very tangible cost: when you’re not working, you’re not making money. As a result, even though you have freedom on a daily level, at a macro level, you’re tethered to your desk. Taking long vacations is already probably harder than you’d like. Heaven forbid you get seriously ill. Who’s going to pay your bills?
Professionalizing your business is the way to solve this. When you go from being a business of one to being a business with multiple employees, the business can continue operating even when you’re not working.
Along with that stability comes different responsibilities. You have to start worrying about things like hiring and managing and payroll. So, again, it’s all a question of tradeoffs and whether or not those tradeoffs are worthwhile to you.
Just remember that, whatever you choose, you’re not forever stuck with your decision. If you do end up growing a successful company, you can step away from it. If you stay independent and get tired of it, you’ll surely have the kind of experience that allows you to get a great job working for someone else. Honestly, the only bad choice would be to not make a choice. Either decide to grow, and go “all in” on growing, or decide to stay working by yourself and commit to that. If you don’t commit to one or the other, that’s when you’ll start running into the biggest problems.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!