26 Lessons Learned From First Time Business Owners

by / ⠀Startup Advice / March 23, 2011


We reached out to some of our most recent Under30CEO Members to ask them about business lessons and surprises they have encountered.  Below are their responses about some of the biggest lessons they have learned while starting their businesses…

1. “The biggest surprise was lawyer fees. I started a clothing company, Twiddy Threads, and through getting trade marks on my designs and logo the bills never seemed to stop. My biggest lesson that im still learning is how important word of mouth is. You can talk about your product all day every day and it seems that no one will hear you. However, have a friend throw in a quick “yeah! these shirts are awesome!” and every one rushes to your store”.–Brad Alderton of TwiddyThreads.com

2. “I definitely was not ready for how quickly everything would take off—I haven’t even been able to finish my website. Being personable and open to letting my business grow a bit organically has lead to offers to collaborate with others in ways that I thought only might be possible after a few years. I keep adding more and more work; I think I’m even working in my dreams now. However, I’m constantly checking to make sure that I’m still doing what I want and not just what’s offered. I don’t think I could ever have prepared myself to love my job this much.”–Anna Sprague

3. “It’s a mighty poor worm that only has one hole to crawl into.-always have a plan A, B, C and heck , even D!”–Crystal Bell – Fresh Start! Cleaning Services

4. “Marketing, I know its something that comes with the territory but it didn’t really hit me until I was in the process of actually developing our business and how important it is for your product. The one thing i have learned is that you have to strategically spend your marketing budget wisely, not all marketing is smart marketing.”–Marcus Brandon – MembersOnlyDevelopment-Group

5. “The biggest lesson i have encountered is Roadblocks. You must continue to come up with ideas to improve the growth of your business. You will continue to learn and make mistakes. The mistakes will teach more than anything else.”–Lasherrick Terrell – Terrell University Staffing  Services 

6. “When I first started my business, I really had no idea what I was getting myself into. Originally, I launched a one-on-one life coaching practice assuming that this was the only service I would ever need to offer. As a member of the expert industry, I need to be much more than just a life coach; I’m also a professional speaker, seminar leader, aspiring author, and online marketer.”–Jennie Mustafa-Julock – Coach Jennie 

7. “Of the hundreds of lessons and surprises, the biggest surprise was the essential need for personal growth.  It is true: your business only grows as fast as you do.  The more educated I became in various areas, the more my business grew.  The more my business grew, the more my desire of knowledge grew.  Now I am ravenous when it comes to reading and educating myself.  As Henry Ford said, “Anyone who stops learning is old-whether at twenty or eighty.  Anyone who keeps learning stays young.  The greatest thing in life is to keep your mind young.”–Maria Joyner – Opportunity & Success LLC 

8. “I was not ready to confront a crisis.”–Samuel Harf of Suprapak.com

9. “My biggest lesson was not to over-promise. Only promise what you know you can do, and keep in mind the timing of other events surrounding your work. I learnt I must be ready to perform in my business ALL THE TIME. Even just after New Years Day, when you’re stuffed like a pig and sleepy as hell, you must perform for your clients as you said you would.”–Emilia Sowden – EMILIAjoan International 

10. “I would have to say that the biggest surprise I’ve encountered thus far is the amount of time that is needed for new business owners. Starting a business requires a lot of time and dedication but you must learn to manage time and balance your business with other events in life.”–Shwan Abdulmajid – Pinnacle Web Services 

11. “The greatest lesson I have learned while in business is you must clearly define all non-monetary parts of your business. Many people spend most of their energy and time on the finance part but you must specify your goals, vision and your service/product. If none of these are clearly defined it will be extremely difficult to execute. You must also do this in your personal life as an entrepreneur, what is it that you are doing and trying to do and why. How will you define success and why? Without these questions clearly answered it will be very difficult to accomplish any of your goals.”–Opeyemi Thomas – CaterTime

12. “The biggest lesson I have learned is the power of determination and persistence. The more we follow up the better the results. In the beginning we were horrible at following up after we sent quotes but quickly noticed the vendors that would call and follow up with us like crazy we always did business with them. Don’t be afraid to follow up because so many people don’t do it.”–Felecia Hatcher – Feverish Ice Cream 

13. “One thing that surprised me was the amount of time I would have to spend working on the business.  I go to school full-time and work 30 hrs a week outside of the business so time is of the essence.  I’ve built a great team around me so even though I have many obligations, everything gets done.”–Larry Lynn – Off Campus Report Card LLC 

14. “One of the most difficult aspects of running a startup business is wearing dozens of different hats and shifting gears constantly as you deal with HR, Finance, Marketing, Operations, Technology, etc…  Yes, you face challenges and uncertainties even when working at a larger company, but those uncertainties are typical limited to your functional area.  Even the CEO of a large company doesn’t have to worry about these things too much because they can delegate problems to their functional heads.  As a startup CEO, however, everything falls on you…and only you.”–Darren Beck – Business Insurance Now 

15. “The competition is always more fierce than you expect and even when you can offer a much better value, getting customers to try something new is an uphill battle. There is a lot of patience waiting for competition to make a mistake, so you can swoop in make a new relationship and create a new customer.”–Josh Nickell – Saturn Security Systems 

16. “Coming from the corporate world, hands down the biggest surprise has been how many hats we have to wear – big picture thinker, project manager, writer, receptionist, accounting department, IT, janitorial staff…  We have a new found appreciation for those roles that had been taken care of by others in previous positions.”–Steve VanPoolen – KreativeMotive 

17. “Don’t outsource your core competencies. In other words, if your website is crucial to your business, for e-commerce companies for example, hire a web designer and developer in-house. It took tens of thousands of dollars and a lot of wasted time for me to learn this lesson.”–Heather R. Huhman – Come Recommended 

18. “The best advice I’ve ever received is that “successful people do the simple easy-to-do things that unsuccessful people don’t do because they don’t recognize them as what really matters” (Rich Schefren). There have been a few times (and that is definitely understating it) where I’m doing a bunch of things that a. aren’t my core competency and b. really don’t seem to be moving me closer to my goal which is the recipe for frustration. However over time those small seemingly insignificant tasks add up and now they’ve become very standard and are useful in the everyday operations.”–Jay Root – Get Customers Right Now 

19. “The rollercoaster ride of highs and lows that you experience on a daily basis – from moments of jubilation at a breakthrough followed by moments of self doubts.”–Natalie Sisson – The Suitcase Entrepreneur 

20. “There are tons of people out there who always talk about wanting to become rich. At many times, it ends up to be simply talk because people aren’t willing to make sacrifices to succeed or aren’t willing to work hard for it. So I discovered that for my start-ups, it is best to rely on my own abilities and dedication or if team-ups are necessary, the partner must be carefully chosen.”–Alan Kong – Alan-Kong.com

21. “You need to think to do every little thing, which isn’t really possible, so you need to be incredibly open-minded, ask questions, and learn quickly. The biggest lesson I’ve learned is to talk to everyone you can about your business, everyone! We all have differing perspectives, so you never know what small, but profound insight a random person might have.”–Edlin Choi – Morning Worm Puzzle Alarm Clock 

22. “In starting my business over the past year I have learned that you must talk to and tell everyone possible about your business.  The more people I tell about my business the more knowledge, networks and connections I have gained.  Originally people whom I felt would have little interest in my business proved to be invaluable resources connecting me with new people who have helped not only my business to grow but myself as a young entrepreneur.”–Brady Lee – I’m Partying 

23. “Actually we are preparing everything. I am kind of a perfectionist, so when it wasn’t ready I didn’t want it to go public. But lately, I got some suggestion from friends and it made me re-think and review all the strategy, I am going to hit the market if I’m ready or not.  It was a good lesson for us.”–Iksan Oetama – Twinkle Witch 

24. “My biggest surprise in starting MyEveryzine is finding you’re still allowed to have an imagination. I was so convinced that upon graduation you had to do everything “by the book.” Though I know there’s totally value in structure, I found out there’s also room to dream in reality.”–Ashlyee Hickman – MyEveryzine 

25. “In starting a business in Africa I realized that a lot of my time had to be spent coaching, managing, mentoring and training my (initially) unskilled employees. It was not something I am used to because in my previous job as a professional I either worked independently or with other professionals. I realized that ongoing personal contact, and having to invest time and energy in another person(s) was time-consuming, emotionally draining and required ALOT of patience. However it was worth it because not only did I myself learn patience and humility in having to work as a team, but all that time and effort also went towards building up a good team which feels like a family – loyal, responsible, and who would go the extra mile for the company. ‘People are not a company’s most important resource, the RIGHT people are!’ (Jim Collins, Good to Great)”–Rebecca Chang – Wamama Kahawa Coffee Roasters 

26. “I was surprised by the length of my sales cycle and how much it can vary from business to business. When you work for a company that has a sales team, you’re not really aware of the sales cycle, but when you are the sales team, the time and work involved becomes very apparent.”–Mikaela Louve – Louve Notes Media 

See also  Human Media Movement: Why Google+ Is a Great Idea For Business

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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