September 12, 2014 | 9 minutes

HARO Submitted post – What is one lesson you wish you could have learned without experiencing it?

By Nathan Strum

While hindsight may be 20/20, learning from the experiences of other’s mistakes can provide valuable insight and lessons to someone newly starting their own business. I recently asked business owners: “What is one lesson you wish you could have learned without experiencing it?” Take out your pens and note paper, and let the lesson begin.

Relationships: The age old wisdom “never do business with friends or family” was brought up by a few respondents…

Alan Katz, President Officiant at Great Officiants shared: “The biggest mistake I made was inviting a friend to work for me. I created a business model and thought my friend would do a good job at it. I trained him how to do it, and he was very good for a time. But, he started slacking and not being as professional as he once was. So I had to cut him loose. In doing so I lost my close friend and he attempted to sue me claiming he owned half my business. The moral of the story is keep your business your business and your friendship your friendships and never the twain shall meet.”

This same sentiment is expressed by Eric C Wentworth who advises: “Never have a partner, even a best friend, without having a detailed and airtight legal agreement first. Doing that would have saved me more than a million dollars…and a lot of emotional pain.” -@AplanForLife

eZanga CEO Rich Kahn further agrees with this sentiment, saying: “Don’t mix business with friends or family. It doesn’t work, and it just muddies the waters of your relationship. It’s hard to be the boss of someone that you have an existing relationship with outside of the office. It destroys the relationship, and isn’t worth it.”- @richkahn

John Crossman, CCIM and CRX for Crossman & Company, also writes on relationships. He says: “My biggest lesson I wish I would have learned without experiencing it was spending too much time in bad relationships and not enough time in good relationships.” – @crossmanco

“I would have been much more successful sooner if I’d made my first hire much 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.” – Barry Maher, Barry Maher & Associates @barrymaher

“I wish I would have consulted with my accountant, my financial planner, and my banker before accepting silent partners with cash in hand.” Says Marty Morua. “In 1989 I was proud to open a nightclub in New York City called Club 281. Several months before opening, I was running out of funds and decided to take on partners- 6 in total. That was the beginning of the end. The grand opening was insanely successful and my silent partners saw this; Greed overcame them, not realizing money needs to be re-invested, employees paid, supplies & inventory ordered, etc. The business lasted for one year.” – @martymorua

Kenny Kline, Founder of Slumber Sage, states: “Sign a contract. By nature I’m very trusting, and with my first company after much struggling, we had landed a very lucrative deal licensing out our software. The software became an integral part of the client’s operations, but we did everything with only a handshake. This license became a significant revenue stream for us, and then the client was acquired by another company. Since we had no contract, the revenue stream was instantly reduced because the larger company came in and renegotiated all terms.”

“I wish someone had showed me how to work with difficult people.” Shares Julia Angelen Joy of Z Group PR, Inc. The ability to bounce back from criticism and the skills to manage negative people are important. We can learn so much from leaders and mentors, but discussions regarding the more delicate issues surrounding office politics, influence, and power struggles are often neglected. – @JuliaAngelenPR

Fellow Shark Tank enthusiasts will recognize the name behind the next piece of advice, shared from Lori Cheek, Founder and CEO of Cheekd.com. “Team is EVERYTHING. I just wish someone had told me the importance of having the right team surrounding me.” @loricheeknyc


Sandra Powers, CEO of LawyerReviews.com adressed education in a lesson she wish she could’ve known- “As an online entrepreneur I initiated marketing efforts with the assistance of outside vendors without looking into industry best practices for SEO. Our enterprise spent a considerable sum of monies only to later learn the tactics we implemented were deemed black hat and our website was unfortunately penalized. Consequently, I have learned to always educate myself in any area in which I lack expertise – even if that means going to the bookstore and purchasing a book – before expending a significant amount of monies for expert advice.” @lawyerreview

Similarly, Lauren Fritsch, a strategist and entrepreneur, responded with a skill she wishes she mastered sooner on in the lifetime of her business: accounting. “I wish I had learned to track cash flow and do regular P&L statements earlier. When I started out I was just a freelancer, taking gigs as they came. But as time went on I got more serious about creating systems for growth and didn’t have a solid handle on my expenses & income. I added contractors and more vendors over time and the P&L became really important but it took me a long time to realize that it could have been much easier if I had been tracking my cash flow better. – @magnetismfactor

Shari Fitzpatrick, found of Shari’s Berries, used to brade about building her multi-million dollar company on $1500 cash advance and passion, and without any business education and experience. Until, she went in on a “bad business deal” and had trusted the wrong person. “I had never learned the 51% rule and didn’t know the importance of doing my due diligence.” – @SharisBerries


Anant Mendiratta, Founder of WorkoutTrends.com shared the value in preparing an alternative: “Those first few years are really hard, and you’re going to mess up. If your business depends on one single client, one single partnership or a small number of customers who pay majority of the bills, then it will be very difficult to survive when the going gets tough.Therefore, having alternative plans of monetization, diversity in revenue and how you can get things done, will be critical for survival. A cushion of experimentation and a plan that can afford a few dumb mistakes will give you the luxury to fail a few times without putting your business at risk.”- @anantmendiratta

Mirroring Anat’s advice, Robin Rothman also shares the power of having a backup plan: “I suffered a very bad concussion back in February and (still) have not recovered because I have so little back-up and have spent 40+ hours/week using computers, smartphone, tablet. I had actually just picked up a huge new project and later had to turn it away. It was embarrassing and unlikely the business will return to me.” – @Robin_R_Rothman

Convinced yet of the value in having a Plan B? If not, meet Christopher Tompkins, CEO of The Go! Agency: “When it comes to key members of staff – always have a plan B. There are many things that you can control as a business owner, but at the end of the day you can’t control human nature. So when a key member of staff suddenly quits make sure that you have thought through a fall back plan so that your business growth doesn’t get derailed.

Entrepreneur John Kinskey shares that he would have “invested more heavily in technology, with more
thorough research into the options available, including on-going support. Having rock solid technology with on-site support would have made early growth more smooth, less stressful and allowed us to focus more of our time on marketing and sales.”


One mistake shared by Stephanie Ciccarelli, Co-Founder and CMO Voices.com was “paying under performers instead of paying ourselves. And to add to the stupidity, we were going into debt ringing up our line of credit to cover this person’s paychecks.” – @stephciccarelli

Andrew Schrage reminded us that patience is a virtue we could all stand to possess: “I wish that I could have learned that patience is important when starting a small business. I spent a lot of time obsessing over the fact that my venture didn’t take off within the first few months, and it caused me a good bit of stress, self-doubt, and concern. Had I known that things take time, the early stages of the development of my business would have gone a lot smoother.” – @MoneyCrashers

Contagious Companies CEO Monica Wofford pearls of wisdom surround the marketing function of your company: “Marketing is a process, not an event” and I wish that saying ‘It seems we are one of the best kept great secrets in the training business’ was not something I almost bragged about for the first few years of our business!” – @MonicaWofford

I can attest to the advice offered by Mickey Mikeworth, as he shares the value in hiring an assistant for your company. “Hiring an assistant as a soloprenuer is about buying your life back. I did not grasp the profoundness of hired help or that putting the right staff on payroll would save me thousands of hours of my life, countless mistakes, and I did not have to always be the first person in at the office.” @prosperityhabit

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