1. “I think I’d have learned to be a manager before I made myself one. I only now am starting to realize how much better I could have been as a manager instead of thrusting myself into the position as a know-it-all. I’ve been running my firm for 23 years and I really only have one regret that is not getting trained in the sensitive art of managing human capital.”
– Richard Laermer, CEO, RLM PR
2. “The transition from a full-time employee to a full-time entrepreneur has been a combination of many accomplishments, but also challenges. The flexibility of working from my home has been phenomenal, but after working almost 20 years for someone else, I realize that an office environment works well for me, even if using co-working space. While I can work virtually anywhere, I am more productive outside of my home and it allows me to maintain a divider between home and work life. If I had to do it all over again, I would have invested in some sort of shared or office space after developing proof of concept in order to maintain the boundary and be able to turn completely off at times.”
– Kimberly O’Neil, Founder/CEO, The Giving Blueprint
3. “If I were to start MyFairyTaleBooks all over again I would have chosen a different brand name. When we started in 2009 we were exclusively selling books. Now we offer many personalized gift items including puzzles, placemats and bookmarks with plans to expand into even further categories. We have such strong brand recognition with our customers that we are hesitant to make too many bold changes to our identity, but we’ve taken subtle steps to share the news that we’re no longer just books!”
– Kelly Mistry, Owner, MyFairyTaleBooks
4. “If I was to do it again, I would have started with the most well known licenses possible and great public domain designs. As it was, in the early days, I was trying to be more thrifty so I went for less expensive licenses. Also, the whole rubber duck industry was invented in America and now every duck is made overseas. We decided to return the whole rubber duck industry to America and had to overcome tremendous difficulties related to lost manufacturing to make this a success. It honestly seemed like a complete disaster in the beginning. But I learned a lot about how to stay the course in a difficult situation by holding onto my dream, not giving up, trusting my instincts, and persevering. If I had to do it over again, I would have done a lot more due dilligence as I had no idea just how difficult it was going to be and the first people we ended up going with just were not able to do what we needed. As Winston Churchill said, the secret of success is going from failure to failure without losing enthusiasm! If you truly hold on to your vision and give it time, in the end you will succeed just as we succeeded. Now we’re the only ones making rubber ducks in the United States for everyone from Harley-Davidson to The Future Farmers of America! We survived and came out a lot stronger for what we had to go through, but I certainly learned a lot of good lessons along the way!”
– Craig Wolfe, President, CelebriDucks
5. “I’d think I’d spend more time considering what I could do or make that could be repeated and scaled up to generate more revenue at the same rate of production. It’s important not only to see increases in revenue but also to have something attractive to a buyer when it comes time to exit the business.”
– Charles Gaiennie, CEO, W.L. Gaiennie Company
6. “August Black was started in 2008 in the height of the recession, and grew rapidly. My business partner and I had to master all skills quickly, and wear all hats at all times. It was from this experience that we learned the skills necessary to manage a fast-paced company in a demanding industry, and to be highly successful while doing it. Looking back, there are certainly things I would do differently. The past 6 years have been a learning experience and we have significantly improved the way things work, which ultimately correlates to how successful we’ve been, and why we have been continuing to grow ever since we began.”
– Charli Hantman, Owner, August Black
7. “I would have implemented a customized CRM system sooner. Tracking your clients’ data is critical to better understand who they are.”
– Joe Ballarino, President & CEO, Amerivest Realty
8. “Instead of wasting months on development, planning and validation, I would have figured out the shortest path to my customer, execute on that path and get my first customer. Learn from my experience, listen to the feedback and rinse and repeat.”
– Pranaya Ghimire, Founder, StartUpLift.com
9. “Absolutely would have not let my private/social life be totally overshadowed by my business.”
– Lynnette Scofield, Owner, The William Henry Miller Inn
10. “If I was starting my business over again, I’ve have taken steps to get good people on board much more quickly than I did. Operating on a shoestring (and a broken one at that), I originally had to do everything myself. The thrift that made it possible for me to survive and then thrive in the beginning, quickly became a hindrance when I delayed hiring people who could do any number of specific tasks easier, cheaper and far better than I could.”
– Barry Maher, Owner, Barry Maher & Associates
11. “If I were to do it all over, I would have picked a better name. Say DivTECH over the phone and the response is almost universal. ‘You’re calling from where? Digitech? Bivtek?'”
– Josh Natella, President, DivTECH
12. “I’ve been in business for over 5 years, and if there was one thing that I would have done differently it would have been to hire salespeople earlier on. I had been doing all of the sales and production in the early days, and by hiring salespeople sooner I would have saved myself HOURS of stress and been able to grow faster.”
– Christopher Tompkins, CEO, The Go! Agency
13. “I would have set aside money for a PR agency to help grow my business, especially for the second year when the name of the business really started to buzz.”
– Fatesta Bateman, Owner, The Spa Bar
14. “When I first started my business, I should have done a lot more research into the legal aspects of owning a business. Corporate entities, taxing, state of incorporation, etc. A DBA just doesn’t cut it. I took the steps to remedy these situations as they came up, which reduced the time I needed to pay attention to the most important thing, running my business. Doing paperwork instead of servicing your customers taught me a major lesson, try to eliminate business hurtles by researching and planning out ahead of time.”
– Robert Garcia, President, iPatioUmbrella.com
15. “I would have begun to build a team of people that I could trust early on and delegate tasks according to strengths and expertise. Running your business as a one woman show is limiting, daunting and leads to burnout.”
– Kimberly C. Thigpen, Founder/Owner, The Bath Place, LLC
16. “Looking back, I would have tried to get an investor involved so I had more backing financially for marketing. There are a lot of free ways to get your product out there but sometimes nothing can replace good old fashioned paid marketing.”
– Jaclyn Kelly, President/Founder, Maggie’s Kids Market
17. “I would’ve carefully watched and monitored my cash flow. When we started, we just assumed business would improve every year and there would be excess to put away and pay everything off. 10 years later, post recession, we are meticulous in our finances and realize had we been smarter in the beginning, we would’ve weathered the economic downturn and probably continued to grow our practice while doing so.”
– Dr. Susan Lowery, Owner, C.H.I.R.O. Health Center, PC
18. “I have been an entrepreneur for slightly over 10 years now. I have enjoyed the good, the bad and the extreme ugly of being a business owner. One thing I would have done differently when I started out would have been to effectively vet who I picked to handle my accounting. In addition, I would have also been more involved in that area of my business as much as I was in growing my business and providing excellent service to my clients. Failure to do this in the beginning created challenges years later. Lessons learned.”
– Monica G. Wood, Lead Strategist, MWPR, Inc.
19. “As entrepreneurs it’s easy to feel like we need to do everything ourselves, but how preposterous is that? I am dreadful at a lot of things, and talented in a meaningful few. If I could go back, I would hire (amazing) people as soon as I possibly could to build the strength of the company, even if that meant eating a bit more Ramen than anyone ever should.”
– Ben Sarma, Operations Director and Partner, Digalytical Marketing
20. “I’m a serial entrepreneur, with 9 businesses to date. If I could go back in time, I would have learned more about marketing and business planning sooner in my career.”
– Nadine Sabulsky, Founder, Coach, Author, Speaker, The Naked Life Coach
21. “Many things I would change but #1 is in regards to hiring. The team you build is critical and you leverage for success since you can’t do it all alone. Some of my initial hires were value detractors instead of additions. I was smart enough to make everyone (including myself) a contractor to start with so it was relatively easy to break off. The other mistake I made was not breaking off as soon as I realized they were not a good fit. Lesson learned: Hire slow, fire fast! I have an amazing team now.”
– Adi Bittan, Co-founder & CEO, Owner Listens
22. “I would have published a how-to book sooner and also created a product. Automation is key to business growth and development. Those selling a service have to work in the business much longer than those selling a product/good. Due to social media and the onslaught of bloggers it has become increasingly harder to tell a story that has not been told or share overly used tips. Timing is everything in business. First to the market in either category (good/service) gains.”
– Isha Edwards, Brand Marketing Consultant & Business Instructor, EPiC Measures, LLC
23. “What I would have done differently is start out adopting the motto we have now: People Before Profit. Oftentimes business owners focus too much attention of turning a profit, which can quickly get you off track. But the key to success is pretty simple: focus on the people first and the profits will come. It’s the same business model Starbucks, Southwest Airlines and other successful companies have. It’s our model too!”
– Nick Cole, Owner, MyNewMama.com
24. “If I had to do it over again I would have allowed more of myself to be expressed in my business instead of trying to fit in in my industry. I am a small business owner but early on I attempted to take on the persona of a corporation from the verbiage on my website, the suits I wore (although I’m more comfortable in jeans), and the type of clients I pursued. It took a couple of years but once I realized that it was more stressful to pretend to be something I wasn’t instead of being myself – my income, influence and peace of mind all increased 100 fold.”
– Summer Alexander, CEO, Summer Alexander Research, Inc.
25. “I would have invested in setting up client follow-up processes earlier. I’ve missed out on a lot of repeat clients by not putting the importance on keeping in touch.”
– Halley Gray, Owner and Marketing Strategist, Evolve & Succeed
26. “The one thing I would have done differently is said yes more often. Lots of missed opportunities and not always about the money. Said yes more often to lunch and coffee, because you never know where a conversation may lead to a new contact, business, or another lunch with more interesting people. Now I say yes more often than not because someone obviously values your company and the conversations can be great.”
– Colin Myles, Author, Colin Myles Publishing
27. “Over the last 4 years of my business we have mastered marketing and lead generation. If I could do it again, I would have started this in year 2 and not year 12. This would have allowed me to build my sales team faster.”
– Tom Malesic, President, EZSolution
28. “The main thing I would have done differently is started sooner. We were first to market in our space, and that has been important. Every day, week, month of advantage makes a difference in the fast-moving software-as-a-service business.”
– Brandon Bruce, Co-Founder, Cirrus Insight
29. “My biggest regret is focusing on perfection instead of just getting to market. As a founder, you want to carry out your vision exactly as it appears in your thoughtful mind which means spending countless hours focusing on trivial details and trying to implement everything you think you know about business. The only way to truly perfect your vision is to try it and test it with your customers. Otherwise, you’re just guessing.”
– Michael Okhravi, Founder, SpoilBox
30. “We would have re-thought our website. We used outsourced technology for far too long. If your website is or delivers on a core part of your customer value proposition, you need to own engineering in-house. This allows you to be responsive, flexible and constantly iterate your product to meet the demands of your customers.”
– Rob Biederman, Co-Founder, HourlyNerd
31. “My biggest regret is not getting rid of weak people earlier than I did in the first few years of my business. I knew in my gut they were not up to snuff but out of loyalty to them I let them hang around much longer than they should have. It would have been better for everyone to let them go as soon as the signs were there. They became more insecure and threatened as we grew which was not productive for the team. As soon as I let them go, the culture got stronger and the bar higher. A-Team people like to be surrounded by other stars. It is true that you should hire slowly and fire quickly. I did not make that mistake again later on so learned it well the first time. Lesson learned!”
– Paige Arnof-Fenn, Founder & CEO, Mavens & Moguls
32. “I was originally a co-founder of Solid Cactus, a company which I sold in 2009 to the Web.com Group, a publicly traded company on the Nasdaq (WWWW). When times started getting tough in late 2008, I did not respond quickly enough to the changes in our business. We were like a family, and I had felt that the changes in the economy had to be temporary. Important changes needed to be made, most importantly, a workforce reduction. Both myself, and the other co-founder, Scott Sanfilippo tried to hold on as long as we could hoping that the economy would improve. My advice is that sometimes changes have to be made and they may be difficult.”
– Joe Palko, Chief Marketing Officer, 3dcart Shopping Cart Software
33. “In my first business I thought I could bootstrap my way to where we needed to be for our next big move. We would need a ton of cash to make the next big move. Despite incredible scrimping, great growth and creativity, it was two years in when I realized there’s just no way to get to the next level by bootstrapping. My optimism kept me from getting a capital infusion when we could best capitalize on it. Worse, I kept the business going for another 18 months because I didn’t want to close a reasonably profitable venture – though it was clear my interests were starting to stray. At this point, I would create strategic capital partnerships despite the extra burden that brings to me and to the business.”
– Kate McKeon, President, Prepwise
34. “The one thing I would have done differently as a business owner is develop a content strategy at the onset. The internet is evolving the traditional business landscape into one that is heavily focused on creating relevant and valuable content for your target audience. We only recently began investing in a serious content strategy and it is beginning to pay off immensely. While content is not our product (we are essentially a research firm that provides experts to legal and financial firms for litigation support, due diligence, and investment research projects), it provides incredible value to the scalability of our online presence and our business as a whole. Our content is our identity and the vehicle to deliver valuable content to our visitors.”
– Michael Morgenstern, VP, Marketing, The Expert Institute
35. “In a previous business, I would have actually spent the time to clearly outline and articulate expectations of one another for the business. Caught up in the moment and good feelings of starting a new business with friends, we jumped right in and split the business 4 ways. However, only two of us are actually doing all of the work, and there is nothing that we can do about it other than dissolve the business. So, in retrospect, it would have benefited me greatly to define those expectations in detail at the beginning.”
– Justin W Boggs, CEO, Signature E-Cigarettes
36. “Every start-up has growing pains, but there are a lot of obstacles that can be avoided by slowing down the pace and spending more time validating your business model in a smaller scale before trying to expand. If I could go back and start all over again, I would be more thorough and careful in testing and validating my technology and service to avoid some of the glitches we faced later on.”
– Jared Erni, Owner, VOAB Marketing
37. “We should have planned for success better, hiring mixologists sooner and having more liquid nitrogen and ice cream base on hand. We also made a lot of purchases that were not necessary, or could have waited. For example, we still would have purchased our killer logo, but we would not have started with a professional website, having mixnmatchcreamery.com take folks to our Facebook page instead.”
– Eric and Genevieve West, Owners, Mix ‘N’ Match Creamery
38. “As a lifestyle brand to chefs and foodies, my customers are my friends, business advisors and critics. They have and continue to shape my business with their insight, purchasing patterns and interest. No matter how much feedback I receive, I can always use more!”
– Alex McCrery, Founder, Chef, Entrepreneur, Tilit Chef Goods
39. “Looking back I would have sought out a mentor to guide me through the initial hurdles of a tech start-up. Having someone in your corner that has walked the walked would have been priceless and educational.”
– Paul Brocky, Co-Founder, TheRoadCode.com
40. “I’ve been an entrepreneur for 10 years, and in the food service industry for more than 30. Looking back, the biggest change I would’ve made would be to intelligently add resources for staffing. I wished I had started my business and added support staff in a more careful and flexible manner, one that didn’t require a compromise of equity or partnership status. After that learning point, I was far more adept at crafting favorable incentive and performance packages when bringing on hires.”
– Ed Doyle, Founder and President, RealFood Consulting
41. “I would have done two things differently:
#1 (Generic): I would not have done everything yourself. Instead, I would have outsourced as much as I can. As a small business, you have ton of things to do and yet you want to be in the market ASAP. I just spent too much time trying to get everything perfect – incorporation, copywriting, marketing, testing. It was just too much for me to handle and as a result increased my time to market.
#2 (Specific): I would have just used online incorporation. I used a CPA. It was just too much paperwork going back and forth and yet I don’t understand how am I supposed to run my Inc. If I just used a good online incorporation site, I would have finished things with few clicks and would have had all my documents in one place.”
– Ravi Duddukuru, Founder, SuperLiked
42. “As an entrepreneur who started a PR firm in 1990, what I would have done differently is taking the time to understand the value of my industry and target market of clientele. I was so eager to have clients, I would solicit my public relations services to anyone who would hire my firm. Now, I understand that you must value your services and be proactive and selective in choosing quality clientele.”
– Parisnicole Payton, Publicist, The PNP Agency
43. “I would stand firm on pricing – yes we all want to be involved in a win-win, but I would be firm and not worry about if the person was going to feel my prices were too high. Instead I would invest that time into showing why I charge the amount I do for PR and believe that if they passed on it – someone else would pick it up and enjoy the benefits!”
– Vannessa Wade, Owner, Connect The Dots PR
44. “I should have been conscientious and made sure that I spent the majority of my time being pro-active rather than reactive. Being pro-active produced the customers in the first place and as time went on I got caught up trying to micro-manage the back-office processing of new inquiries on daily tasks. If I would have made myself spend 80% of my time being pro-active and increasing the new business it would have forced me to find a way delegate or simplify the other tasks and I would now be seeing a much larger business that is far more profitable. The pros would have far outweighed the cons.”
– David Bird, Online Mortgage Advisor, OnlineMortgageAdvisor.co.uk
45. “I didn’t plan cash flow by month. The challenge was that I didn’t take into account receivables that would slow my cash collections. While I ran a slight profit, I didn’t have enough cash to operate. I had to add more cash into the business- which created a personal financial strain.”
– Ken Boyd, Owner and Founder, St Louis Test Prep
46. “The saying patience is a virtue is definitely something I wish I took more seriously when I was starting out. As a younger entrepreneur I was always ambitious on the hunt for more. Over time I realized that results don’t come over night in many cases, instead they take time and effort but when they kick in, they are that much more valuable. I’ve come to realize this now and have adjusted my thought process going forward but I can’t make up the time I had spent doing things differently.”
– Stanley Meytin, Creative Director/Owner, True Film Production
47. “I would have sold products first before building them. We ended up building a lot of functionality and throwing it away because we did not try to sell it for real money before we built it. There is a difference between what people like and what they will pay money for. Moving forward, I will get MOU or pre-payments before putting in lots of effort in building the product. Ability to sell your product for cash is the real product market fit.”
– Brahm Kiran Singh, CEO, Coach Pal
48. “I wish I’d known sooner that I could, and SHOULD, delegate the things I wasn’t good at and that it would actually save me money in the long run! In fact, it normally ends up making me money If you love what you do, recognize that you won’t get to do that full time in your own business. I love coaching, but need to spend the majority of my time running, marketing and selling my business in order to get to coach.”
– Elene Cafasso, Enerpace, Inc. Executive Coaching
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