I was an entrepreneur for two weeks. Here’s what I learned.

A month and a half ago I took a new job as the Online Marketing Manager for Hotpads.com, the nationwide apartment and condo rentals subsidiary website of leading real estate website Zillow. I gave my notice at Distilled and finished out three and a half weeks there. I start my new job Monday.

In between though, I’ve had two weeks off. Originally, I took those two weeks off to potentially travel. I was hoping to go to Ireland to visit an old friend from my 2006 Switzerland days, but flights were prohibitively expensive. Instead, I decided to stay around New York (though I’m writing this on a plane to Colorado before heading to Seattle and San Francisco) in order to see the city some more. To be honest, I didn’t do much of that though I did take an afternoon to go to the American Museum of Natural History (true fact: Theodore Roosevelt’s family opened it).

Instead, I worked on my side project HireGun. Here’s what I learned.

Entrepreneurship is a mindset

I was an entrepreneur full time for these two weeks. You might be thinking “Dude, you still have no idea about entrepreneurship then.” And you might be right. I have no idea about the legalities of entrepreneurship, I’m just learning about book-keeping and invoicing (I do recommend Freshbooks though), and I haven’t built a full product yet. I have a website and a business model that I’m in the process of testing.

However, this isn’t all entrepreneurship is. Entrepreneurship is a mindset. Entrepreneurship is a dedication to identifying problems or opportunities, trying to fix them, and changing the world for the better. If you’ve made one person’s life better, you’ve been successful. If you’ve made some money great. But that’s not all entrepreneurship is. Entrepreneurship is identifying challenges and dedicating yourself to shipping things to try to make them work.

I didn’t realize that until this week. And honestly, I think the entrepreneurship mindset is closer to a creative mindset than a business mindset. You can learn business strategies, processes, and models. You can’t really learn creativity. And this is why I claim “Entrepreneur” in my Twitter profile.

Entrepreneurship is hard and scary

If I didn’t have a new job that I was heading into, and one that I am very excited about and where I see a lot of opportunity, I might have been a nervous mess these past two weeks. Having to think about budgets, prioritizing features and tasks based on what you think will bring in ROI, and then making deals – this is hard and heady stuff.

If I had a family, I would’ve been even more nervous. I have an apartment to pay for, food to buy, and a girlfriend to treat to things, but that’s very very different from your venture being your sole source of income.

I don’t know how a lot of you do it. I plan to do it someday still, but I’ve definitely had a reality check. At the end of the two weeks though, I was Ramen profitable. I consider that a win.

Test your business models

Business models are tricky. It’s tough to realize that the model you’ve been working off of has flaws and you need to put in more work to figure out if it’s a completely viable option or if you need to tweak or even completely change your model. Early on is the time to test your business model, because without a solid revenue model in a bootstrapped business you will quickly run out of runway and will not be able to scale.

The past two weeks I’ve been testing my model. I’m not convinced I have it figured out, and if the one that I think will really work is to succeed it’s going to involve a lot of time and effort. We’ll see what that turns into.

Lesson – even if you’re making money, you don’t necessarily have your business model figured out. Test other ways and do the math to figure out what will be long term profitable and sustainable.

Talk to your customers and ask for help

Your customers are your greatest asset. In HireGun’s case, the greatest asset is the strong lineup of consultants on board that I refer business to. When I realized one of the roadblocks to my business model, I could have gone one of two routes. I could have immediately started executing on what I *thought* would be part of the answer, or I could ask consultants if that would be valuable to them.

I chose to do the second. I sent an email with the subject line “Do you have 15 minutes to chat?” I explained that I had an idea that I needed to run by them and asked for just a few minutes of their time. This is the email that I sent – simple and straight forward with a call to action at the end:


I set up the calls through Clarity.fm (see my interview with Dan Martell, the founder, here). They handled all the logistics and I was able to do all the calls for free through their offering. And as you’ll see in the next section, I gave specific parameters for when I would do the call so that I could have blocks of time to do other things (like exercise).

Lesson: read The Lean Startup. You’ll learn how to test ideas.

Vary your day and batch your work

I get bored easily. If I keep at one task for too long, especially while sitting (which I’m convinced is slowly killing us), I get bored and antsy. So, I tried to schedule out my day so that I could reach peak efficiency – sleep in a bit, do some writing in the morning while I’m fresh and drinking coffee and eating a healthy breakfast, check for new leads and contact them while still drinking coffee, eat some lunch, go on a bike ride for at least an hour around Prospect Park, come back and answer more emails, do some outreach or publish content, check for new leads with a beer, then unplug for the evening.

On days where I was doing calls, whether with consultants or paid gigs through Clarity (my profile here), I set parameters for myself for when I would be available. Then, I stuck to those. I marked off the afternoons on Wednesday and Thursday of the first week for consultant calls, then I scheduled paid consulting calls on the next Wednesday. In between, and other times those days, I had time to either have to myself (to read or write) or choose to not work at all if I wanted/needed to refresh myself.

This approach to work is often called “batch working” or “time boxing”. Basically it’s a way to guarantee that certain tasks won’t take over your life and not allow you sufficient time to do focus and do anything well. It’s a strategy I employed as a consultant (no calls before 10am, etc) and one that I plan to employ at Hotpads too in order to allow for maximum productivity.

Get some exercise

It’s counter-intuitive, but scientific, that exercising gives you more energy rather than less. Sure, you’re spent afterwards but your adrenaline is flowing, and I’ve found that it’s often these times after exercising that I am the most creative. I used to ride my bike into work, from Park Slope in Brooklyn to Union Square in Manhattan, and it was these days that I was most awake (needed less coffee) and also the most productive.

I recognize that not everyone has the luxury of exercising in the middle of the day. I have friends in finance who are barely able to leave their seats in order to go use the bathroom because they may get a call to make a trade where every second matters.

If you are not in the habit of exercising, start slowly. One reason that so many people do not succeed in their New Years Resolutions is because they set them too high and go too strong. Commit to going for a walk two times a week. Soon you can take that to three, then four, and soon you’ll crave going for a walk to clear your head.

Final Thoughts

This was a great two weeks. In fact, it’s two of the most enjoyable I’ve had in a while (definitely since my trip to Alaska back in June). I’ll take these lessons into Hotpads and beyond. If any of you have experimented like this and written about it, I’d love to read your stories too.

6 thoughts on “I was an entrepreneur for two weeks. Here’s what I learned.

  1. “You can’t really learn creativity”

    false. the more you immerse yourself in a creative environment and surround yourself with creative people, the MORE creative you become.

    1. Agreed that you can become more creative, but I believe that there are creative people and not creative people. If you had a disposition to it, you’ll become more creative. If you don’t, you won’t and you’ll be frustrated by the process.

  2. Great article and well worth a read for any budding entrepreneur. Good luck at Hotpads.com hopefully you will still be out and about on the speaking circuit!!

  3. two questions –

    what do you plan to do with hiregun once you join your job? Will it remain a side project or are you keen on growing it further?

    How does one join your list of consultant? what is he criteria?

    1. Hey Brandon – thanks for reading and the comments! I totally plan on keeping HireGun going and will invest time in it as I can. It’s growing and working, and I’d love to keep pushing it forward and automating as much as possible.

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