21 Big Risks That Produced Big Payoffs

Taking calculated risk is a large part of starting and growing a business, and it comes in many different shapes and sizes.

If you are the type of person who cringes at the thought of taking chances, entrepreneurship will push you to stretch your wings from time to time. Last week we wanted to hear your best story and asked:

What is the SINGLE BIGGEST RISK you’ve taken in your business, and how did it really PAY OFF in a BIG WAY?

Whether taking a chance with their finances, firing clients, or delegating responsibilities, find out what our entrepreneurs were willing to risk for a big payoff in their businesses by reading on…

From the responses we received this week, you will see how risk can vary, but still pack a big punch. Discover how Amber Schaub mustered the courage to just say “no” (#6), why Ian Aronovich had to rethink his company’s pricing strategy (#8), and what happened when Richard Houston went against the grain in his industry (#21), to name just a few.

Our sincere gratitude to the 21 entrepreneurs who shared the stories of their biggest risks that really paid off. Openly providing your expertise and experiences is a huge asset to this blog and the readership. I wish you all a wonderful week and hope to see you here again.

If you would like to contribute to the next post and get some free PR, be sure to scroll all the way to the bottom of this post to discover this week’s question and find out how you can get involved.  We’d love to have you on a future post!


1. The Sky Is The Limit

After having my second baby, I needed to do something drastic to be able to be a mom and run my successful jewelry business. I wanted to make more money for less work. So, after almost 10 years of selling wholesale through a sales rep and trade shows and being in top stores such as Anthropologie, Henri Bendel and Fred Segal, I decided to stop selling to stores and focus primarily on selling retail on my own website.

It was a huge risk, but worth it. When a celebrity wore my jewelry or my designs were featured in a magazine, my website was credited instead of other stores. Web sales sky-rocketed and I was making the retail price of each piece which is 2x the wholesale price. It also helped grow me and my name as brand.

Thanks to Maya Brenner of Maya Brenner Designs

2. No Pain, No Gain

I happen to be shy and quite unassuming by nature. I had to go against my natural tendencies to network and actually reach out to other small business owners.
The payout has been incremental over time resulting in more branding opportunities for my business, cross promotion and sales.

Thanks to Bola Ajumobi of Slimy Bookworm

3. Stepping Into The Unknown

At the beginning stages of my business, I was with a hosting site that I was paying a monthly fee, and a little extra for email campaigning and etc. I was struggling with the spending the money to get an ecommerce site. I was not ready to give up that kind of money, even though I know I would greatly benefit from it. I would have complete control over my website, and more flexibility, where as to my previous website hosting company, I did not have control. Well, after struggling with leaving my comfort zone, January, 2011, I cancelled my old site and switched companies. I must say that this was one of the biggest risks thus far, and now looking back on it, I’m glad I now have complete control over my site, and I stepped into the unknown with a positive mindset and outlook.

Thanks to LaTersa Blakely of Baby Diaper Cakes & Beyond by LaTersa

4. The Biggest Risk Was Hot & Wooly

I needed inventory to start my business 16 years ago (a retail store of imported Tibetan handicrafts & local art). I had made some good contacts in Nepal at the Tibetan Refugee Camp, but I still had to place a large order, 100% prepaid. I ordered mostly sweaters..gorgeous, hand-knit, but very hot and very wooly (smelling). I used all of my start-up capital on that order without anything to show for it. I was freaking out for about eight weeks, until a truck pulled up at my tiny shared apartment in Jamaica Plain (Boston). There were my sweaters, and a bunch of other stuff…and soon I was off selling out of the back of my car.

That business became my current company 6 years later and we are now approaching eight figures in sales, shipping nationwide. It was a big risk but it worked out!

Thanks to Richard Sexton of Carolina Rustica

5. Personal Growth

The biggest risk I took was starting the business itself. It was clear hours of dedication were needed, and the calculated payoff was not quite what was expected (money/earning a living). Instead of money, I’ve got something to hand my children, something I can say I accomplished that no one can take away from me, and my work can continue to touch people’s lives long after I’m dead. I’ve actually found what I love doing, after college crushed all the dreams I thought I had, and despite the hours upon hours, I still love doing it. Biggest risk: Committing, and jumping off that bridge. Not completing college. Not exactly seeking a job. Biggest payoff: Finding what I love doing, spreading goodness to the world, accomplishment, and an inheritable knowledge base for my offspring.

Thanks to David Majlak of DIRT-FTW

6. “NO”, My Biggest Risk

My single biggest risk since starting my company has been saying “no”. I have always been a yes person, but when the day came that a VERY large retailer called interested in carrying our products, I had to follow my gut and take a risk…I told them thanks, but no thanks. This has turned out to be one of the best decisions that I have made. We have since grown our brand and our business, and most importantly, we now have a much better grasp on who we are and the confidence in our bigger vision.

So, my advice is not to turn down business, but to always follow your bigger plan. Many times this requires taking a risk.

Thanks to Amber Schaub of RuffleButts, Inc.

7. Going For Broke

I was always an employee of the safest kind: a public school special education teacher. When teaching no longer was an option for me, I found I had moved all over the country but had no pension like my peers have. I did an inventory of my skills and what types of jobs would be appropriate, but teaching was all that I really excelled at. Initially, I intended to take the “safe” route for a small business by tutoring. The schools now offer after school tutoring for free, so my business venture had to change. I decided to replicate myself because I had learned how to help children make enormous gains. The challenge was how and the result is a web page that gives parents information they need to know as well as offering training on how they can help their children.

Thanks to Jennifer Little of Parents Teach Kids

8. Pricing Model Change

The single biggest risk we’ve taken at our company was to change our pricing plan because we didn’t know the outcome. Originally, we offered a $39.95 annual membership with no trial period or opportunity for recurring payments. After our membership growth plateaued, we decided that we needed to rethink our business model. We came to the consensus that we were going to change our membership plan to a three-day free trial and then an $18.95 monthly recurring fee. This helped us garner a whole new crop of members because people were interested in the information we provided, but they didn’t want to commit to a full year without knowing what they were getting. Thankfully, this new system was exactly what our company needed and our membership is consistently growing day by day.

Thanks to Ian Aronovich of GovernmentAuctions.org

9. Transition From The Minor To The Major Leagues

After hearing that some regarded me as a “minor league player,” I decided to take a huge risk: I went after a contract with a Fortune 100 company….and won it! That victory, of course, convinced me to seek other Fortune 100 contracts. I was successful in all but one of my attempts. Transitioning from the minor to the major leagues requires courage and resiliency. But, if you have that true-grit American spirit, you should tell yourself each day, “Take me out to the ball game!”

Thanks to Dr. Marlene Caroselli of Center For Professional Development

10. I’ve Fired Clients

I’ve actually gone through and fired several of my clients at different points in my business. It’s been an incredible risk each time, but I knew those clients weren’t going to be up to the next step my business was taking (such as a rate increase), so I went through and let certain clients know that our contract was coming to an end. It’s scary to not have a full slate of clients, but every time I’ve taken this step, I’ve actually wound up with even more clients.

Thanks to Thursday Bram of Hyper Modern Consulting

11. Subcontractors, Not Employees

Because I enjoy the creative aspects of public relations so much, when I founded my PR business I decided not to hire employees and instead work as the lead on every project with a team of talented subcontractors. New Mexico Business Weekly currently ranks my company the Number 10 PR firm in our state.

Thanks to Jane Blume of Desert Sky Communications

12. Fly Without A Net!

Biggest risk? Going full-time in my business without funding and without a safety net. Knowing that my livelihood depends on my ability to make my business succeed. I chose to not get a job, part-time or full-time, and devote every ounce of my energy to making my business work. It was terrifying, but ultimately worth it.

Thanks to Lauren MacEwen of SM Cubed Consulting

13. Going Beyond Limits

Being a part of the corporate world for many years, I suddenly realized that I was an entrepreneur at heart. I have an extreme ability in serving others, encouraging others, leadership, and bringing together like-minded professionals. As I thought of what my business development coaching and consulting would look like, I made a decision to invest in a licensure program as a foundation. This was a costly program, and could have been a huge risk. To the contrary, it gave me the resources I needed to move forward with conviction. As a result, I have been able to double previous earnings. Realizing my personal fulfillment, my sustained motivation, and enabling the success of other business owners is my true pay off.

Thanks to Shirlie Taylor of Business Success Dynamics

14. Less Can Be More

In our family daily car rental business we made a decision to reduce our ‘Yellow Page’ ad to half & then reduce our fleet from 70+ vehicles down to 48 vehicles. The thinking was that the excess of cars we had in our fleet was needed to pay the difference in the size of the ads. We would still have a sizeable enough ad & if we were correct, we would make as much money with the smaller fleet. Having a smaller fleet, we could keep our pricing stronger.

It was a gamble because if it did not work, we would get killed financially that year untill we could build up the next years fleet with next year’s models. It was a win-win. We worked easier – had less damages to deal with – fewer employees & had made more money. It was a tight run ship & when we eventually sold it, it was easy to do.

Thanks to Harris Glasser of Serving The People Press LLC

15. Six Figure Pay Cut, Well Worth It

Realizing that even though I had a very successful business, if I wanted to take the business to the next level and really grow it going forward, I would have to make major changes that would cause me to take a six figure pay cut. Knowing that I wanted to sell the business within six years, it was imperative that I make these changes now to increase the value I would receive at the time of sale. So, I made the necessary changes including letting all of my staff go, hiring and training new staff and putting the money that was necessary back into the business which came directly out of my pocket, to improve systems and efficiencies. Within 24 months, the business was better than it had ever been. We had more clients, more efficient systems and my income was the highest it had ever been.

Thanks to Nancy Butler, CFP®, CDFA™, CLTC of Above All Else, Success In Life And Business

16. A Bigger Risk Than Gambling

Being 26 years old and a former professional gambler, many would guess my obvious answer would be simply the act of accepting the position of CEO of the rapidly growing social media platform.

I had a team full of experienced business heads, people with resumes made of gold and years and years of experience on me. However, the ability to trust in someone else to complete mission critical tasks for my company was something I didn’t feel comfortable with.

Eventually I realized that I needed to take the plunge. I delegated tasks, allowed my team to work and focused on my list of mission tasks. My biggest risk proved to be the smallest risk and best move I’ve ever made business wise. The team shined and our company’s growth and productivity shot through the roof. Implications to those reading this: build a strong team and allow them to fully utilize their expertise and potential.

Thanks to Jason Lee of Jaspud.com

17. Never Hurts To Try!

I loved original hand drawn animation art and was a dealer in this genre, so it was a huge leap to tell Coca-Cola that I could develop a whole line of animation art using the computer generated images from their Polar Bear commercials. I spent thousands on R&D to deal with all the intricacies of creating this art, plus getting the licensing rights. I also had no idea what I was doing and was learning on the run. But it paid off as I became the largest publisher of animation artwork from television commercials in the country. Then I thought I would try my luck again and create a whole new art form of licensed celebrity rubber ducks. It was again a big gamble, as no-one did such detailed work. We’ve since sold over a million ducks and were voted one of the top 100 Gifts by Entertainment Weekly!

Thanks to Craig Wolfe of CelebriDucks

18. Get A Credit Card

When I started my Internet Marketing Company I sold everything I owned to get business capital, which wasn’t much because I just graduated college. Then I supplemented my capital with a business credit card. I bought everything I needed to help my clients. The risk paid off when I increased my clients’ online sales, and they all renewed their campaigns with me. I was able to pay off the credit card and have a sustainable business, all because of taking a risk.

Thanks to Pavan Katepalli of Bloggers Compete

19. If You Build It They Will Come

As a Wedding planner with a new business, I wanted to educate myself further on selling and marketing to brides. So I searched for wedding industry conferences, educational and networking events and found none specific to wedding businesses. Finally, I realized that I would have to go abroad to attend one or organize it myself.
I was bold, contacted the big expert names and flew over a great speaker, organized the venue, a website, and started email and social media campaigns. I had the industry’s attention, but it was a new concept and no one wanted to spend the money to attend. My target market was extremely skeptical. I did a few contra deals to up the numbers but was terrified I’d be there alone having coffee with my speaker.
In the end, attendance picked up and it was a successful and highly praised event instead of a financial ruin. Now, everyone in the industry knows my name and my company and this year’s event has 3 speakers and 2 dates in different locations!

Thanks to Annie Byrne of Aislinn Events

20. Branching Out

The single biggest risk I’ve taken in my business is offering to purchase the business from Intuit. Having served as the general manager of the division I now own, under Intuit, I understood the business, the product line, the customers, and the employees. When the economy hit a rough patch, my division had a tough time competing with the other priority businesses within Intuit. As a stand-alone business I thought this division could make the necessary changes it needed to fit within the economic framework of the time, and could retain a great partnership with Intuit. This was risky. How could I do this on my own, outside of Intuit? Well, I had the great support of the Intuit team, the employees of my division and my family — that’s all you really need.

Thanks to Deborah Sweeney of MyCorporation

21. How To Profit From Goldman Sach’s Recommendations

Most of us traders off Wall St. know better than to follow Goldman Sachs’ recommendations to the public. So when one of their analysts put out a buy recommendation on LA Gear near its all-time high of $55, I immediately bought some put options and on every up tick, I would buy more. When the stock started drifting down into the high $40’s, I called a friend and found out he was doing the exact same thing. Within a few weeks, the stock had dropped into the low 20’s. It was a Friday and I had to go into an all-day meeting, so I sold out my whole position for a profit of $145,000. At the end of the day, I called my friend and he told me that the stock had dropped to $7 and trading was halted right after he sold out for over $1 million in profit. SEC lawyers finally believed us!

Thanks to Richard Houston of Lawsuit Jackpots.com

Thanks so much again to all our wonderful contributors for sharing your biggest risks and how they paid off! We hope to hear from you again.

If you are new to the Question of the Week and would like to get involved, simply follow the link below to get started. We’d love to have you share your knowledge and experiences here too, and get a bit of PR in the process.

This week’s question is –

Best Live Event for Entrepreneurs

Every year there are live events around the globe focused on blogging, social media, entrepreneurship, empowering women, etc. Investing in live events can be game changing through the training, making new connections, expanding your vision, and being inspired or challenged by others.

What was the single BEST live event you attended in the past 12 months that you would highly recommend, AND what made it a life changing experience for you and your business?

(Please avoid the temptation to plug your own event, as we are looking for recommendations from your personal experiences.)

Why should I join the discussion?

Because this online forum is a great place for us to exchange ideas, learn from each other and network. My goal is to unite successful women entrepreneurs to share our insights and solutions to the challenges we most commonly face in our businesses.

How do I get involved?

Every Monday I will post a new Question of the Week. This is a great opportunity for you to bring your expertise to the table. Using the link below, please submit a one paragraph response before the deadline, and the following week I will share our community responses on my blog.


I look forward to your response to this week’s question! If you have any questions you know where to find me. Have a great week!


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  1. Posted August 22, 2011 at 12:46 pm | Permalink | Reply

    I have taken too many big risks to list here. Some were a great success (but often not the way I expected them to be) and some were total disasters. I don’t gamble in the traditional sense but I get a great kick out of taking risks as an investor or entrepreneur. I think to be successful as an entrepreneur you have to have little fear of failure and think nothing of starting all over again, this can be learned or conditioned or you can be born with it. I wrote an article a while ago called formula followers http://mattkinsella.com/2011/03/30/formula-followers/ about people who don’t like risk but don’t get far and those that can do things differently and get much further in life.

    • Posted August 22, 2011 at 1:26 pm | Permalink | Reply

      Hi Matt! Thanks for sharing your comment here and the link to your post. The point is that you took the risks, whereas so many are afraid (and I was one of them) to take the leap. But you never will know how amazing you can be if you never take the chance to find out. I would probably be categorized as a “Formula Follower” for most of my life. But I was able to break free from the mold and break into a new life and direction when I finally focused all my attention on what God put me on this planet to do. And it’s been a total adventure every day since. 🙂

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  1. By Build a Better Business Today - Omnia Veritas Blog on August 25, 2011 at 12:51 pm

    […] Risks these entrepreneurs took to make their businesses better. The biggest lesson in building a small business is that there is no success without risk. That risk may not always be financial in the form of investing lots of money in your startup. Here are some examples of the risks business people just like you made to grow their businesses. Dr. Shannon Reece […]

  2. By Build a Better Business Today | NSD Newsletter on August 23, 2011 at 6:09 am

    […] Risks these entrepreneurs took to make their businesses better. The biggest lesson in building a small business is that there is no success without risk. That risk may not always be financial in the form of investing lots of money in your startup. Here are some examples of the risks business people just like you made to grow their businesses. Dr. Shannon Reece […]

  3. By Build a Better Business Today on August 23, 2011 at 5:01 am

    […] Risks these entrepreneurs took to make their businesses better. The biggest lesson in building a small business is that there is no success without risk. That risk may not always be financial in the form of investing lots of money in your startup. Here are some examples of the risks business people just like you made to grow their businesses. Dr. Shannon Reece […]

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