#54 Lessons from Year Two

JOHN ACKERMAN SITS DOWN AFTER HIS TAX SEASON HIATUS TO DISCUSS THE LESSONS HE LEARNED FROM YEAR TWO IN BUSINESS.

While we sometimes forget, we actually have a millennial entrepreneur as one of the hosts of Drunken Money (me). I just wrapped up my second tax season as a CPA out on my own, so we decided to kick off Season 2 of Drunken Money with Paul and I discussing what I learned from year two as a full-time entrepreneur. This is: Lessons from Year Two.

• When you're on your own, there are periods of time when you must work nonstop to make sure your business is successful.
• To get started in Year One, I called family friends I knew who might use my services, and relied on word of mouth to grow from there.
  • I overcame initial fears of quitting my job by constantly reminding myself "What's the worst that could happen?" In many cases, the worst case scenario is just going back to your prior job (most of the time higher up than when you left because of the experience you gain while you're out on your own).
  • My plan when I started was to make money within  5 years (break even the first 4 years), and rely on my wife's (who is awesome and super supportive - which is the biggest reason I can work on my own) income to survive the first few years.
  • The biggest surprise I encountered was how busy I stayed year round (accounting is a very seasonal business but there is a lot of work year-round to get ready for the busy seasons).
  • For many entrepreneurs, if you do good work, you will get more clients than you initially expect. In my case, the 8 or so clients I started out with slowly grew through word of mouth. There were also friends and acquaintances I wasn't expecting to get as clients who called me up to do their work.
• Sales strategies
  • Paul (who is very successful at his job), has a huge network he has developed and is a terrific salesman.
  • I do not like to sell and am not a huge fan of networking events, but I think if you do good enough work for your clients and they trust you/know you have their best interest at heart, your business will grow organically.
  • Also, Drunken Money has done great things for my business as well and has really given me an outlet to market my services without constantly making sales pitches.
• Process of hiring employees
  • This was the most difficult part for me from year one to year two.
  • In total, I had four people helping me this tax season, after never managing employees before, and had to learn how to juggle multiple projects at once along with multiple employees' schedules.
  • Instead of focusing on one project at a time from start to finish, I had to learn this year how to shuffle multiple projects along at the same time to make sure the projects all were completed by the due dates.
  • Luckily, everyone who helped me this year had a fantastic attitude and was eager to learn.
• Managing Expenses
  • From year one to year two, my expenses increased dramatically due to payroll, rent, and additional computer equipment/software because of the new employees.
  • I went from working out of my house by myself to working out of an office with support.
  • One thing this resulted in was me not being as conservative with my billing and to bill what my time was worth instead of trying not to offend clients by billing as little as possible. I now have many more expenses I must pay for to keep my business open, and need to make sure I bill enough to stay in business. 
• Purchasing an office
  • This process took a few months to complete - if you are looking for a space for your business, make sure you leave enough time to close on the space and leave time for renovations before you move in.
  • This was a game changer - as it really made my business more legitimate in the eyes of many clients and gave me a place to always have meetings instead of coffee shops.
  • I'm a big fan of working from home, but nothing can replace having a permanent physical office for necessary meetings and to legitimize your work.
• What is the most important thing an entrepreneur should focus on?
  • Make money and turn a profit.
    • The most important things are not publicity and marketing, it is making money and being able to have a business and not just an idea.
  • If you constantly give away free work (which was my biggest mistake my first year), people will keep expecting you to give free advice and will devalue your work.
  • If somebody thinks your bill is too high, at least in my case, it was often because I did not give a good enough explanation to them about the detail I go into. It is not simply plugging somebody's information into a computer, there is much more analysis, review, and advice given than what many people initially realize. 
• Getting clients and people to believe in you and the work you do is one of the most rewarding things as an entrepreneur.
  • For me, it was getting old teachers from college as clients my first year that really made me feel like I could be successful out on my own.
• What advice would my 60 year old self give me today?
  • Work less
  • It's a very common answer for entrepreneurs to feel like they work too much, and I have to keep reminding myself to work less and to enjoy the moment each day. So often you try to rush to the finish line instead of enjoying the process. 
• What would be my dream job?
  • Chef - I loved Emeril growing up!
  • As Paul noted, my tag line if I was a celebrity chef would probably be "Can we make it vegan?"

SPECIAL SHOUTOUTS AND SHOW NOTES:

• Wild Turkey
• Green Man Brewery
• Alex Wright - Payroll Solutions
• Nikki Chin
• Tarik Nally / Kale & Flax
• Rework
• El Mundo

Have any topics you want to be covered or amazing people you’d like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.