Business Owners: If I Had Known Then What I Know Now

I’ve made many mistakes in business as a business owner the last 20 years.  There was a time in the beginning when I thought that I had all of the time in the world.  But now I feel like I can’t afford the luxury of wasting precious time anymore by making costly mistakes.

If you’re like me, you’ve probably said this statement many times: “If I had only known then what I know now.” I understand that mistakes are part of the process, but do I have to make so many of them!?! Experience has made me a fast learner and now, more than ever, I pay attention to those who have gone ahead of me so I can learn from their mistakes and hopefully not make so many on my own. Maybe you do too.

To gain some more insight, I asked business owners who have been in business five years or more the same question, “If you would have known then what you know now, what would you have done differently and why?” Their answers were not only insightful, but inspiring and I think you will really appreciate what these owners had to say.

So here you go: 30 insights from business owners like us on what they would have done differently had they known.

We would love to hear your answers too, please leave a comment and let us know, “What would you have done differently in your business if you would have known then what you know now.”


1. Hire slowly, fire quickly

Oh man, I wish I would have remembered this one every day when I woke up. There is little of greater importance than having the right people on your team(s) and when you find out an apple has gone bad or you have found a worm in a seemingly perfect apple, get rid of it ASAP! The old adage is often true, “some dogs can’t hunt.”

Thanks to Ben Sayers, VoIP Supply, LLC. VoIP phone systems, in business 8 years

2. Be more open to change

Technology and trends are constantly evolving: one day you are set in your Facebook ways and the next day Pinterest is the new phenomenon. Social media has changed the way we do business and how startups utilize it is integral to your success. However, if someone told me this during social media’s infancy, I would have called them crazy. I let all my years in business bias my first impression of social media and thought it was simply a fad. I couldn’t have been more wrong! Social media has changed the way we do business and has set the bar for the way we measure success. If companies are not willing to adapt, they will never become an industry leader or experience great successes.

Thanks to Jim Joyal, SHIFT Communications, PR and social media agency, in business 9 years

3. Be the boss, not the buddy

Don’t be friends with employees. When you try to be too nice it makes it easy for others to take advantage of you, and that’s been true of about 80 percent of everyone I hired in the past. There was a time when I would give a job to almost anyone who asked, regardless if they were qualified or not, because back then I had the capital and I did not want to be the person who turned them down. Most of the money I lost when I started out was due to being overly tolerant of inefficient employees. It’s fine to be friendly with your staff, but owners have to set boundaries and be willing to be a firm boss — whether you have three or 300 people working for you.

Thanks to Cathy Ward,, wedding accessories e-commerce retailer, 11 years in business

4. Lock in your location

Had I known then what I know now, I would have done everything possible to purchase my own business property. Last year, the rent for my original office, located in the Prospect Heights section of Brooklyn doubled, necessitating my having to move during my income tax preparation season.  If I had to rent a property, the lease would have included a “lease to own” clause and have a termination date during my slow season.

Thanks to Eustace L. Greaves Jr., Greaves Financial Services, Insurance and Income Tax Preparation Services, 17 years in business

5.  Start with sustainably in mind

In hindsight, I would have focused much more deeply on a sustainable way to generate deal flow and new leads. No matter how large owners think their network is (mine is large) it is not large enough and although power networking/word of mouth is the best source of leads of all the advisor/coach/consultant/solopreneurs I know almost none are reaching their personal income goals. What I am doing differently is focusing on the internet. I have just launched an e-commerce site and hope to launch a content site in the next 90 days. Historically my advisory services were delivered on site at companies located regional. I will continue with my advisory work with about 1/3 of my time, but focus on national and to a lesser extent international clientele via phone or Skype.

Thanks to Ajax Greene, On Belay Business Advisors Inc., business advising, 7 years in business

6. Know the value of vision

I would have placed an earlier emphasis to define the vision, mission and values of our company. It is important for the value of our employees to be aligned with my vision for our company.

Thanks to Jason Maxwell, MassPay Payroll Services, payroll services company, in business for 8 years

7. Eliminate Distractions

Having owned several companies, I would have eliminated my distractions sooner than I did, e.g. real estate investments (rentals), buying and selling a laundromat, renovating homes, etc. While all the ventures were profitable they took away from focusing on building a brand that ultimately would have had more value than the combined profits of each transaction not related to directly building that brand.

Thanks to Joseph Carvelli, Retail Ingenuity, retail inventory and sales forecasting, business owner for 12 years

8. Set aside significant savings

I assumed if I built a good product, they would come! I had no idea how costly being in business would be, the amount of money I needed to succeed or the toll the financial strain would take.

I am blessed that I had the tenacity and the strength to succeed despite overwhelming odds. If I could go back to the beginning, I would make sure I had significant savings set aside, or capital from another source. I cannot overstate the importance of being properly funded!

Thanks to Regina McRae, Grandma’s Secrets, dessert delivery, in business for 18 years

9. Put more emphasis on processes

If I had known then what I did now, I would have put a lot more time into creating processes. I find that with the majority of businesses these fundamentals often get overlooked and sometimes ignored completely. To me this is utter madness! A company can succeed or fail just by their processes. We find that we avoid 99% of mistakes because we process them out. This not only avoids unnecessary errors and client issues, but actually makes the company as a whole more efficient.

Thanks to Ben Norman, Koozai Ltd., UK based digital marketing agency, in business for 6 years

10. Delegate, delegate, delegate

I would have delegated more and not tried to do everything myself. Although it does take time to build relationships with your staff, I waited too long to delegate certain responsibilities that could have been done by someone else. Giving responsibilities does much to validate a staff member’s gifts and also demonstrates a deeper level of trust in the employer/employee relationship. Letting go of certain tasks has been difficult for me but I have come to realize that the more responsibilities I entrust to others in their areas of expertise, the lighter I feel, the more confident a staff member becomes and greater things are achieved by their efforts than could have been done otherwise.

Thanks to Stephanie Ciccarelli,, online voiceover talent marketplace, in business for 8 years

11. Let go and let it grow

For many years, I had to know everything and do everything. I have discovered that other people and organizations can do things better and at a lower cost than doing it myself. Letting go has enabled my business to grow and prosper and made my life much easier.

Thanks to Bob Shirilla, Keepsakes Etc. and Simply Bags business owner for 30 years

12. Avoid delaying difficult decisions

My biggest lesson over the years was learning that sometimes decisions had to be made for the good of the company, which sometimes meant disciplining or dismissing employees. In particular, when the economy started going into recession, I had to fire one of my closest friends in order to keep the company going. I should have done it sooner. As a result of my delay, it took a while to regain the company’s financial stability. Making difficult decisions is part of owning a business. Owners have to be willing to do it.

Thanks to Susan Southerland, Just Marry, Just Right DM and The Susan Southerland Secret, event planning, destination management and small business consulting, in business for 20 years

13. Start with a solid team

I would have started with a solid business plan, hired an account and started with a solid team around me. There are not many businesses that are successful with one person wearing so many hats. Do what you do best and allow others to contribute what they do best to help your business grow.

Thanks to Amore Leighton Black, Apples & Oranges Public Relations, public relations and marketing, in business 7 years

14. Charge what I am worth

I would have charged more! I was so excited to be working for myself doing something I loved. I’ve never been a person who chased profits -that’s not why I do what I do. But I didn’t do my homework and when I started, I charged pretty close to what I was making hourly at the jobs I’d left behind. That was all fine dandy except when working for myself, that wasn’t enough to cover things like taxes, health insurance, and so on. And also, I was definitely undervaluing my services. I was booked ALL the time, yet I could never seem to get ahead. Even though my clients all loved me and thanked me for my work, I doubted my value, and that was definitely reflected in my pricing.

Thanks to Alaia Williams, One Organized Business, professional organizing and small business systems consulting, in business 5 years

15. Focus on building relationships

We spent a fortune of money on advertising when we started out (with unimpressive results). We then changed our focus on relationship building with existing clients and organic search maximization vs. paid ads.  Now we see incredible returns in the form of referrals, and new business at a cost that is a fraction of what we used to spend. We needed to learn the hard way but if I knew then…

Thanks to Ben Schusterman, ElJet Aviation Services – private jet charter service, in business for 5 years

16. Start with more money, fewer friends

I would start with about three times as much cash as I thought I needed. I’d also be cautious around hiring friends/family.

Thanks to Heidi Ganahl, Camp Bow Wow, doggy day & overnight care, in business for 12 years

17. Use a better business model

If we knew then what we know now, we would have started with the business model that we changed to about two years ago. Before the recession hit, we charged $39.95 for an annual membership with no free trial, and no automatic rebilling at the end of their membership term. During the recession, the rate in which we generated new members waned and we reached a growth plateau. To combat our stagnation we decided to change our revenue model to a free trial and a monthly rebilling combination. We implemented a three-day free trial and then a recurring $18.95 monthly fee after the three days expired. We are doing very well as a company now, but in retrospect, we should have thought about rebilling from the get go.

Thanks to Ian Aronovich,, providing information about government auctions of seized and surplus merchandise

18. Hire employees sooner

One thing I would do differently if I were starting my training business today would be to make my first hire sooner. Operating on 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.

Thanks to Barry Maher, Barry Maher & Associates, motivational speaker, leadership trainer

19. Dream bigger

I would have dreamed bigger from the start. In the beginning, my focus was on serving clients in my own Puget Sound backyard, even though successful people who were familiar with my publicity expertise and storytelling gifts were telling me to think nationally or globally. If I had it to do over again, I would have put more emphasis on national and global reach of my message right from the start.  Lead with juicier, higher value, and leveraged offerings first. When I was just starting out, I put a lot of emphasis on creating the absolute best $10 product about do-it-yourself publicity that I could create. Yes, the Media-Savvy-to-Go Publicity Tips Booklets have sold by the thousands since debuting in August of 2006. However, it is so much easier to make a bigger impact for more people and my own balance sheet by leading with a juicer, higher value offering. Today, the Broadcast Your Brilliance Webinar Series and Bye-Bye Boring Bio PLUS! Programs deliver great value for many around the nation and the world at price points that make it a whole lot easier to make a good living. Whether you create an entry level product or something much more, you still have to create all the systems to support those offerings. By leading with a deeper offering, the rewards are greater for all.

Thanks to Nancy Juetten, Authentic Visibility, PR tools and training, in business 11 years

20. Approach additional services more cautiously

I’ve been in business as a web designer for 18 years. The main thing I would have done differently knowing then what I’ve learned along the way is I would approach any add-on services very cautiously. I used to briefly check out add-on services such as hosting, domain name management, and others, and then I would jump in wholeheartedly. Most of the time, it worked out fine for me. However, the occasional missteps cost me dearly.  As I learned more about running a business, I also learned through hard knocks that it is much better to approach additional services methodically and cautiously. I don’t put a lot of funding and energy into them until I’m sure it is the right thing to offer. I’ve learned it is easier to resist the urge to jump at opportunities than it is to extract myself from the occasional quagmire!

Thanks to Jim Smith, Blarneystone, LLC web design, in business for 18 years

21. Give more away sooner and speak more

Network a lot more in person (the Internet was in its commercial infancy) and hunt for in-person speaking engagements, even if they are not paid. Good writing alone is not enough to convince clients to hire you. They want to hear you speak on your topic of expertise, and when you help business owners with their problems or concerns, they are more likely to hire you and/or to recommend you to others who hire you. I once helped a business owner write something for his church at no charge, and with another small assignment that paid very little. That led to a long-term writing assignment that exceeded $40,000 in fees. Sow seeds of goodwill and interest through your networking, speaking and help. Continue to do this even after your business is successful because it leads to more success.

Thanks to Candace Talmadge, Talmadge Writing Services, writing services, in business for 29 years

22. Been more focused on this business

I wouldn’t have started it out of my apartment. I would have “cleared the decks better” by parsing other interests that I was juggling at the same time. I would have learned more about guarding a business (legal, insurance, LLC/Scorp/Inc).  I would not have spent so much money on a business plan.

Thanks to Todd Greene, HeadBlade men’s grooming, in business 12 years

23. Don’t do it all yourself

I would have gotten an assistant, accountant and web coder much earlier. I did it all myself for 8 years in my business and have only been hiring assistance for the last two years. I knew it would free up my time to hire people – and what I didn’t know was how much it would free up my mind and let me do better, more powerful work along the way. I’ve been able to create more products and do more thought leadership since getting those little tasks off my plate… and if I’d done it earlier, I can only imagine how amazing things would be.

Thanks to Erin Ferree, BrandStyle Design, branding for small businesses, in business for 10 years

24. Look before leaping

What I know now is the huge cost of marketing and promotion required to build demand. We started out expecting to sell retailers and distributors and attend trade shows and travel to customers and sell and spent two years on that path. Then we took a hard right and for past two years we have evolved into an Internet retailer running DRTV (Direct Response TV) infomercials with 85% of our business now direct to the consumer. Social media was never in the business plan either, but now it’s vital.

What would I do differently knowing what I know now? (1) Keep my old job as long as possible and not leap off the cliff (but it was a nice feeling) and (2) Anticipate 5 years to break-even, and set aside “don’t touch” money.

Do I regret jumping off the cliff? No way. As I tell my wife: Don’t look down, keep looking up!

Thanks to Brad Barrett, GrillGrate, LLC, grill surface for better food, in business 5 years

25. Pick more profitable partnerships

I would have used deeper discernment in picking partners/vendors/joint ventures, even markets. I picked some doozies AND, after the fact, saw all the red flags.

Thanks to Shawne Duperon, ShawneTV, media coach and production company, in business 11 years

26. Focus on face-to-face interactions and new technology

We learned a lot of lessons in starting our company. For example, we would never produce four-color mailers that are sent to mass prospective clients. We’ve learned that face-to-face interaction and building the business relationship is key. (This was pre-Internet.) We also learned that a lot of mailing lists are not updated. This endeavor was expensive and resulted in a poor ROI. When the Internet came around, we certainly would have jumped on this new technology much earlier — developing a website much sooner. It’s an amazing tool to get your message out to the world to sell products and services with visuals. We try to make it much easier for clients to find us rather than we search for a needle in a haystack to find prospective clients.

Thanks to Greg Jenkins, Bravo Productions, event planning and production company, in business 25 years

27. Plan for growth, be more discerning in following advice

As the owner of a driving school in New York City, my first big regret is that I did not get all other licenses (Motorcycle, Bus, Truck license) earlier in life. I just passed my truck road test Tuesday, Jan. 17, 2012.  Now I have to wait two more years before I can expand to teach Truck Lessons thanks to an NYS requirement. Secondly, I was too naive and trusted many so-called experts who convinced me how to run my business only to find out they were wrong.  I wasted a lot of money trying ideas that did not work. 3. In the real estate boom time, I should have purchased commercial real estate to accommodate my growing business. Now it’s impossible to get a loan. I would have preferred to spend a bit more money to secure a property.

Thanks to Rajendra Hariprashad, Ena’s Driving School, in business for 8 years

28. Leverage people, build a system

If I knew then what I know now I would have invested in two areas. One, I would have developed other people and brought them into the business sooner. No one is good at everything. Even Michael Jordon had a coach and teammates. One of my friends started a business five years ago and has 700 people working for him today. The more you can leverage other people and create a ladder for them to achieve what they want to then the more successful you will be. Find people you can trust and learn to work effectively with them. My business is much stronger today because I have a strong team.

Secondly, every business needs a system to build a pipeline that is consistent and measurable. I have depended too much in my business on my farming method, which is delivering exceptional value to people I meet and eventually they and their friends become clients. I wish I would have understood how to build visibility for my business in my target market like I do today. I am beginning to develop a hybrid model that is both farming and hunting, which I believe in the long run will deliver greater growth to my business. My approach that involves taking a prospect from visibility, credibility and trust is proving to be highly effective. When people work with me, they become more than clients; they become friends because I am invested in their success. Every day owning a business is a learning experience. I am very happy it is what I have chosen to pursue in my life.

Thanks to John Paul Engle, Knowledge Capital Consulting in business 10 years

29. Focus on building relationships with customers

When I first started out, like most new veterinarians, my prime concern was my patients and their care. What I failed to fully appreciate was that each patient had an owner (aka client) attached to it! Often I would not address the needs and concerns of the client as well as I was trying to practice medicine and over time, I likely lost clients who, if I had better built my relationship with them, would still be a client today.

Thanks to Dr. James Day, Glendale Animal Hospital, veterinary practice in Glendale, Arizona, in business for 27 years

30. Establish boundaries with employees

I would certainly separate “church and state” and I would have been more of a leader than a friend. As an owner and an active president and  CEO of a small business, I’m in constant contact with my employees. When hiring new employees, certain requirements and credentials are necessary, including experience, expertise and industry knowledge. Additionally, I look for multiple interpersonal skills and qualifications. That said, I’ve managed to find and retain wonderful employees who work well and who work well with one another. Formulating good friendships with my employees is nice but maintaining and stepping up as more of a leader at times has been challenging. Establishing boundaries early on with employees is key for owners and I wish I had known the importance of this, earlier on.

Thanks to Georgette Pascale, Pascale Communications, LLC. a health care specific PR firm, in business 7 years

Wendy Kenney is the bestselling author of How to Build Buzz for Your Business available on, and has been featured in the Wall Street Journal, USA Today and Newsday.

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