• Tommy Holstein

5 Important Lessons From One Year of Entrepreneurship

Updated: May 27, 2019

It’s one of the scariest things you can do, but it’s so damn enticing.


Entrepreneurship is like playing the lottery: the odds are stacked against you, but if you win, you can win BIG. Unlike the lottery, though, there are many things you can do to increase your chances of success.


Everyone knows that most new businesses fail. The Small Business Association says that about 33% fail in the first year and about 50% in the first five. In March of this year, my business hit the one-year milestone. The doors are still open, phew. Even though we’ve survived this long, though, there’s still a long way to go before we reach what Les McKeown calls “Predictable Success”.


To beat the odds, I’ve become obsessed with learning why most new businesses fail, and the steps I can take to avoid it. I don’t by any means call myself an expert; I’ve not been doing this long. There are TONS of people who know a lot more than me and have been doing this a lot longer. But I’m learning. As Gary Vaynerchuk says, “If anybody who looks like you has ever done it, you can too.”


So you’ve got the audacity to try to start something? Good. That’s lesson number one.




Start Now


When I was a freshman in high school, I decided I wanted to play roller hockey. My younger brother had started playing, and I was a bit jealous. Admittedly, I didn’t join because I loved hockey or anything, I just had never played a sport and didn’t want to graduate high school without having played one. I was very hesitant at first, though. I didn’t want to embarrass myself, so I wanted to practice on my own and build up some skills before I hit the rink.


My Dad talked me out of this mindset.

“Tommy, if you wait until things are ‘perfect’ before you start, you’ll never begin.”

This is one of the biggest lessons my father instilled in me. There was no time to wait. I just had to jump in and do it.


I had my first hockey game before I had even had my first practice. I didn’t know how to handle the puck, and I barely knew how to skate. Sure, it was embarrassing. But I got better. And I loved it.


Just like playing hockey, the first rule I learned in business was that there is never a “perfect” time to start. It doesn’t matter how many internships you have, how many books you read, how many seminars you attend. You will never be “ready”, so you just have to start.


It’s Not Who You Know, It’s Who Knows You



We’ve all heard the phrase, “It’s not what you know, it’s who you know.” I’m not a huge fan of this phrase. It implies that your knowledge and skill sets won’t get you where you want to be; that you have to know somebody that can give you an opportunity. I prefer the phrase, “It’s not who you know, it’s who knows you.” I view this in two parts: building your network, and building your audience.


Building Your Network

Since graduating from college, I try to have coffee with a new person at a minimum of once a month. I joined my local Chamber of Commerce, I attend conferences, I DM people in my industry on Facebook, and just try to meet as many interesting people as possible.


This is your traditional networking, but doing so with intention. I’m uninterested in going to a networking event with the goal of just handing out as many business cards as possible. Rather, I seek out specific people who I am interested in and try to build an actual relationship with them.


Simply handing your business card to somebody means nothing if you don’t follow through. If you exchange information with somebody at an event, and you think you could benefit from that relationship, try to set up a one-on-one meeting with them at a later date. Invite them to lunch, learn about their life, find common interests. Focus on building a friendship before you try to start a business relationship.


Building Your Audience

This one is all about gaining people’s attention online and delivering valuable content. What is it you’re trying to do in business? Who kind of audience are you trying to attract, and what kind of content do you think they could benefit from?


This is specifically what I do for a living. I own Holstein Studios, a content marketing agency based in St. Louis, MO. We create content for businesses to attract and build an online audience.


We do this by focusing on two pieces of “pillar” content — videos and blogs — and then creating “micro-content”, smaller pieces of content that are repurposed from the original videos and blogs.


I recommend the book Content Inc. by Joe Pulizzi if you are interested in starting this for yourself.


Don’t Be Afraid To Pivot


For the entirety of 2018, my focus was to create videos for businesses. I spent the entire year cold-emailing every business I could find to try to sell video services.


I landed a handful of clients, and by the end of the year, I was making three times the amount I was making per video at the beginning of the year. I was thrilled to have successfully scaled up my pricing, but I was still broke. I realized that even if I was raising my prices, it was just too much of a hassle to try to hunt down the next client over and over again. It also wasn’t very scalable. I knew I needed to make a predictable income, and my business structure didn’t allow that.


At the beginning of 2019, I changed to a long-term model, where we create content consistently, not just a one-and-done project. In doing so, I am now able to allocate funds in the right places, and I know exactly what I need to do and how many clients I need to reach certain milestones in my business. It’s no longer a guessing game of how much money I’ll bring into the business each month, it’s just a matter of how many clients I’m working with at the time.


For the longest time I felt that if I changed my business at all, I would have failed to reach my goals. The thing is, nobody knows exactly what they’re doing the first time around.


It’s completely okay to change the way you do business, to try something else. You should always be analyzing what you’re doing, and ask yourself, “will this work in the long-term? Is this sustainable?”


Be honest with yourself, face your challenges head-on, adapt your business to reality, and you’ll do just fine.


You Don’t Know What You Don’t Know


If you think you’re done learning when you’re out of school, you’re not going to get very far. I think I’ve actually read more books in the year after I graduated from college than the entirety of my college career.


When I started my business, I didn’t know a single thing about how to run a one. As far as I was concerned, all I had to do was make as much money as possible, and that was it. As long as I could make good videos, that’s all I needed to succeed.


Boy, was I in for a rude awakening.


In the past year, I’ve had to learn so many things that I didn’t even think about when I started. Bookkeeping, managing client expectations, search engine optimization, social media algorithms, just to name a few.


After the first two to three months, I felt like I was in way over my head. Who was I to run a business? I had never even taken a business class! I started a business without knowing the first THING about running one! What was I thinking!?


Out of necessity, I introduced reading back into my life. I grew up reading almost daily, but back then, it was just for fun. Now, I’m learning. I’ve learned about the 7 Habits of Highly Effective People from Stephen Covey. I’ve learned about the myths we tell ourselves about entrepreneurship from Michael Gerber. I’ve learned how to overcome the largest obstacles in business from Les McKeown.


There is so much to learn, so much that it can be overwhelming. Here’s my advice:


1. Set reading goals.

Give yourself a set time each day that you want to read. 5 minutes is better than 0, 15 is better than 5, 30 better than 15, and so on. Build this into your daily routine.


2. Get a list of topics you want to learn about.

You’re not going to learn everything at once, so make a list now about what things you want to improve on. Find the top recommended book from each category and add it to your list.


3. Write down the top insights from each book.

If you buy books, write all over them. Underline, star, circle, whatever you have to do. If you use the library (highly recommend), make a spreadsheet of the most important information you’ve gathered, and where you learned it from.


4. If you don’t like it, put it down.

There’s no point in finishing a book just for the sake of finishing it. If after two chapters you think, “I’m not really getting much from this book,” move onto the next one. If you’re not enjoying it, you’re wasting your time.


If reading isn’t for you, no problem. There are tons of free videos, courses, and other resources you can find online. Whatever you do, just don’t stop learning. If you do, you’ll stop growing.


One Plus One Equals Three


I feel like not enough people talk about this, so let’s start here: ENTREPRENEURSHIP IS LONELY. If you’re on a mission that nobody’s joining you on, you’ll get so lonely. You’ll spend hours and hours by yourself, with nobody to talk to, to really talk to, about what you’re going through. Sure, you can share what you’re working on with friends and family, but they won’t understand it as you understand it.


If this sounds like you, I highly recommend getting a partner. I promise you, even if your business is your “baby” and you don’t want to share it, you will be eternally grateful to have somebody to join you on your crazy ventures.


For starters, you can get so much more done when working as a team. Obviously, with two people to share the workload, twice as much will get done, right? I’d argue it’s even more than that. When you have a partner, you have somebody to bounce ideas off of, to brainstorm with, to encourage you. That last one is the most important.


Before I added my business partner Dillon to my team, there were so many days where I’d say, “Eh, I’m my own boss! I don’t have to work today if I don’t want to!” After we became a team of two, we started encouraging each other to be better. If I see Dillon working hard, it makes me want to work even harder, and vice-versa. After just a couple of months working together, we made an ENORMOUS amount of progress, more than I could have anticipated.


And seriously, it makes it a hell of a lot less lonely.




Bonus Tip: Don’t Quit Your Day Job (Yet)


The first job I got out of college was a gig waiting tables at a restaurant.


I had a couple of interviews to be a video producer or motion graphics designer at a couple of different companies, and I even had two offers. I stuck with the serving job.


I don’t know if I’d exactly recommend this route, but it was my path, and it worked for me. I knew that if I had a full-time job, it would be a lot harder to grow my business. So, I opted to work just as much as I needed at the restaurant to pay my bills, and the rest of my week would be spent building Holstein Studios.


Now, this worked for me because I didn’t have a mortgage or kids to take care of, and my student loans hadn’t even kicked in yet. I had very few bills, and I made it work.


I knew that if I could work solely on my business, I could grow it a lot faster. But, I also knew I couldn’t just “jump ship” without enough cash. So, I told myself I would work the restaurant job until I was making enough through my business to replace the money I was making there.


It took an entire year.


Every Friday, Saturday, and Sunday night, I walked out the back doors of that restaurant and thought to myself, “in a year, it’ll all be different. I just have to keep pushing.”


I’d be lying if I said I never thought about giving up. I had those thoughts quite often, actually. I specifically remember a conversation I had with my Dad, one month before I landed my biggest client yet — the one that allowed me to quit the restaurant job. I told him I was tired. I was tired of feeling like it was going nowhere, that I was wasting my time. I was just going to pack up shop, get a steady job, and actually put my degree to some use. My Dad said,

“Tommy, if that’s your decision, I’ll support you 100%. I think you should give it a week or two to think it over. Is there anything you could be doing differently? Any change you could make in your business that will help you succeed?”

Thank goodness we had that conversation. A month later I had a new business model, I’d quit my job at the restaurant, and I had a new fire burning inside me. I was ready to take on the world.


We’ve got a long way to go, of course. We’re still a team of two, working out of a home office. But we’re on our way.


In a year, I’ll look back on where I’m at now, and it’ll all be different.


I’m looking forward to that moment.

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