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“People Can Achieve So Much More If They Stay Focused In One Area And Go Deep” With Author and Entrepreneur Carol Roth

“My favorite exchange was with a gentleman who reached out to me via email in a time of need. He was working three part-time jobs and was…


“My favorite exchange was with a gentleman who reached out to me via email in a time of need. He was working three part-time jobs and was at wits end. I wrote him a short mail of encouragement and thought nothing of it. He emailed me back almost 3 years later to say that my note had given him a spark and he was now the first person in his family to have landed a six-figure job. You can read the entire exchange here, but I didn’t think much of the gesture. It was small, like throwing a pebble into a river, but the ripples it created gave him what he needed in that moment and it was a big deal for him. That’s what makes me feel good and I am privileged to be in a position to do small things for people who may need them even more that one could imagine.”


I had the pleasure of interviewing Carol Roth, the creator of the Future File® legacy planning system, “recovering” investment banker, billion-dollar dealmaker, investor, entrepreneur, business advisor, national media personality and author of the New York Times bestselling book, The Entrepreneur Equation. Carol “plays herself on TV” weekly, having been a reality TV show judge (Mark Burnett’s America’s Greatest Makers on TBS), media contributor to outlets ranging from CNBC to Fox Business, and host of Microsoft’s Office Small Business Academy. She’s recognized internationally as a business expert and has worked with startups to the biggest companies and brands in the world on everything from strategy to content creation and marketing to billions of dollars in capital raising and transactional work. Carol is dedicated to helping families prepare for and save the time, cost and grief that comes with aging, medical issues and passing life events through her Future File products, and is also a former public company director, noted small business advocate and influencer. Carol counts among her “accomplishments” having an action figure made in her own likeness, getting a standing ovation from Richard Branson and having the NFL follow her on Twitter.

Thank you so much for doing this with us! What is your “backstory”?

I grew up with parents that didn’t graduate from college. My mom- who was like Martha Stewart crossed with Cher- was a full-time mom turned hobby entrepreneur. And my dad- who was somewhat like if you crossed a Jewish grandmother with a mobster personality- was a union electrician and also very financially savvy.

I was able to get accepted to Wharton undergrad at the University of Pennsylvania for college but had to pay most of my own way through school since my parents didn’t have much money, and even less as they had initiated a divorce. I worked and pursued entrepreneurial endeavors (there may or may not have been a football pool involved…) to make as much as I could to live on. I graduated Magna Cum Laude with $40,000 in debt in 1995 and knew my first task was to pay it off. The fastest way to do so was to take a job in either investment banking or management consulting right out of school. If you like to go really deeply into something, consulting is great. But I get bored easily, so investment banking allowed me to work on a bunch of deals at once, and I pursued that route.

I paid off my debt in a year and a half, while living in a tiny studio with a cardboard box with a sheet over it as my bedside table. That discipline allowed me to make my first million dollars by age 30. I was very successful at investment banking, but it wasn’t something I wanted to focus on, so I decided to morph my career, which has been an ongoing evolution ever since. I also met my fantastic husband and life partner in the company gym almost 21 years ago and we have been together ever since, with our 19 year wedding anniversary this fall.

Over the 23 years I have been working post school, I have also been a public company director, bestselling author and author of thousands of pieces of content, speaker worldwide for some of the biggest companies in the world, an adviser to the biggest companies in the world and many small businesses as well, an advocate for small business, a reality TV show judge, a business and current events commentator, a radio host on a major market station and so much more.

Truthfully, I’m still figuring out what I want to be when I grow up.

In addition to the fantastic accomplishments and experiences, I have also had a lot of issues to contend with. I think this is important to talk about, because these are the things that most people don’t get to see — the struggles. But, the struggles make you even more of who you are. I have had a lot of loss to contend with, including losing my boyfriend in a car accident at age 21 my senior year of college, followed by my mom being diagnosed with Leukemia shortly after I started my career. She passed the day after her 51st birthday. Then, my step mother was diagnosed with lung cancer and passed at age 55.

The stress from these gave me several debilitating, undiagnosed illnesses, including IBS and gastro issues. They got so bad that at one point, I couldn’t bend over to touch the floor. Despite never knowing what they were, I have learned to manage them to a livable point.

The biggest blow was the loss of my father, who was also my best friend — we talked around 3 times every day — five years ago in a freak accident. That’s created some health issues too, but again, I push through. He was the inspiration of my current entrepreneurial endeavor and product, Future File.


Can you share the funniest or most interesting story that happened to you in the course of your career?

I have been blessed with so many funny and interesting experiences, from having to become an auctioneer at a conference when the real auctioneer didn’t show up, to laughing onstage with Shaq during a TBS show we both judged to interviewing businesses leaders like Richard Branson and Bank of America CEO Brian Moynihan.

But, the story that probably tells the most about me is how I got my first job in investment banking. At Wharton undergrad, many institutions recruited on campus. As I figured out which firms to apply for an interview with, I realized that there were several firms from San Francisco, which I had never been to before. I also knew that if you did well in the interviews, the firm would fly you out to their location, at their expense, for final rounds of interviews. So, I applied with a San Francisco based investment bank called Montgomery Securities purely to try to land a free trip.

It turns out that the interview was scheduled for the same day that I was competing in the Miss Illinois pageant (my one and only and very random experience with that!). So, I had the nerve to call the recruiter and beg for another way to interview because my investment banking interview was conflicting with pageantry.

The recruiter was somewhat amused and told me to call back a few days later. Every time I called trying to find another way to interview, he kept telling me to call back. On the 17th try, he finally said, “You are the most persistent mother****er that I have ever met, and so I am going to grant you an interview.”

I went up to NYC to meet with a Vice President and had a great interview. Ultimately, I did make it out for my free trip to San Francisco for a final “Super Saturday” of interviews. Funny enough, I didn’t love the city, but I did love the company and decided to forgo working for one of the big investment banks in New York City to be part of this fun, aggressive growth, meritocracy-based company. This worked out incredibly well, as I made it to Vice President myself by age 25 and met my husband in the company gym.

But, the story shows that persistence and not being afraid to embarrass yourself or ask for something can really pay off. It also shows that sometimes, you never know where the opportunities may come from!


How have you used your success to bring goodness to the world?

One of the reasons I went into the small business space was to provide entrepreneurs high level advice by media that they couldn’t otherwise afford. Through my books, articles, online shows, speaking and other endeavors, I have heard from entrepreneurs that weren’t ready to start businesses say I have saved them collectively millions of dollars with my advice. I have many others that I have helped make successful.

However, my favorite exchange was with a gentleman who reached out to me via email in a time of need. He was working three part-time jobs and was at wits end. I wrote him a short mail of encouragement and thought nothing of it. He emailed me back almost 3 years later to say that my note had given him a spark and he was now the first person in his family to have landed a six-figure job. You can read the entire exchange here, but I didn’t think much of the gesture. It was small, like throwing a pebble into a river, but the ripples it created gave him what he needed in that moment and it was a big deal for him. That’s what makes me feel good and I am privileged to be in a position to do small things for people who may need them even more that one could imagine.

If someone would want to emulate your career, what would you suggest are the most important things to do?

Definitely don’t emulate my career [laughs]! Seriously, you’d be crazy to do so. I advise to “do as I say, not as I do”, so to speak. I think people can achieve so much more if they stay focused in one area and go deep to accumulate experience there.

But, if you are a “Renaissance Man” or Woman at heart and like to collect experiences, what allowed me to do so many different things was setting a strong financial foundation first. The absolute best thing that money can buy is flexibility. I stayed in investment banking until I had enough financial flexibility to do what I wanted, which was key to allowing me the time to be successful in new endeavors. It’s hard to go off on a tangent if you are struggling to pay your rent or mortgage.

Also, I have an amazing partner in my husband. We pursue our goals as a team and we made a conscious decision that we were both happy with — that he would continue to work in more traditional roles (translation: having a very steady income stream), while I pursued different entrepreneurial endeavors.

Is there a particular person that made a profound difference in your life to whom you are grateful? Can you share a story?

The person that has had the most profound effect on who I am had to be my dad, Bernie. He led by example with his amazing work ethic, getting up at 4:15 am everyday and often working outside in sweltering heat or below zero temperatures for 40 years to provide for his family. He still found time to be very involved, coaching my sister’s and my softball teams, teaching us skills and sports, sharing financial lessons and more. He opened up a credit card for me when I was just a youngster to establish my credit history! He always supported our endeavors and never gave us any limiting beliefs. He felt if we wanted to do something, we could.

I remember when I was 12, I wanted to attend our local day camp for the summer. My dad signed me up to work in the kitchen of the day camp instead. I literally made at least a thousand peanut butter and jelly sandwiches every week! But, it taught me the value of work, having my own money and also what I didn’t want to do later on (i.e., that kind of repetitive, task-driven work). He definitely shaped my confidence and personality.

So, what are the most exciting projects you are working on now?

I’m working on a few different “TV” formats with production companies, including two that include me as “talent”, which are exciting in theory, but I always temper my excitement, as the majority of those projects tend to fall apart. Of all the projects that I have been involved in over the years (and there are many), only one has made it to network so far. Hollywood operates very differently than the corporate world, so I am still trying to get my head around that.

But, my most exciting project is a mission-based product that I launched called Future File®. Future File is a legacy and wishes planning system that gives you a roadmap to organize your wishes and information related to aging, medical emergencies and death and then provides a roadmap to your loved ones, including all of those wishes and information in one “grabbable” location should something happen to you.

This was born out of personal experience, as my father created the prototype of this product for my sister and me after my mom passed from Leukemia at age 51 and my stepmother from lung cancer at 55. When he was in a freak accident 5 years ago, we had to use this file to find his power of attorney and wishes related to being in a coma and when he didn’t make it, we used it to wrap up his affairs. Having it saved us a lifetime of burden, more than $10,000 and hundreds of hours trying to track down all of his information, policies, accounts, valuables, etc.

As we told other people about this product, the feedback was that they needed it for their loved ones, whether aging parents or grandparents, spouses and partners or children. So, we created it to deal with everything from things you need to know related to aging to wrapping up affairs after someone dies. It allows those left behind to access wills, powers of attorney, aging care wishes, funeral plans, financial accounts, spare keys, social media accounts and wishes and so much more. Our mission is to help and prepare as many families as possible, so I hope everyone will get one for themselves and their loved ones!

What are your “Top Five Ideas About How Influencers Can Monetize Their Brand” . (Please share a story or example for each.)

I was very early to the influencer “game” when it was in its infancy around eight years ago. Over the years, I have both acted as an influencer myself for some of the most noted brands in the world, as well as investing in an influencer platform that makes it easy for brands to connect with influencers at scale.

In terms of monetization, here are 5 ideas for influencers looking to monetize their brands that extends past just typical online posting.

1) Speaking: Having a notable and influential brand is a great conduit to a speaking career. Speaking is fantastic because, for those who are willing to hone their messaging and delivery, it can pay very well and add longevity and credibility to your brand.

As an expert, you have interesting content to share, so to pursue speaking, you need to create 1 or 2 signature speeches that are around 45 minutes in length. As businesses, colleges, membership associations and more hire a wide variety of speakers, from motivational speakers to those who can give tips on sales, marketing and leadership, make sure to weave your story in with key lessons and takeaways. If you aren’t sure where to begin, go to other conferences to see some keynote speakers and also do searches online, as some speakers put their content online, too. This will give you some good ideas and models.

Make sure to add a speaking page to your website, mention that you are a speaker, add your topic in your social profiles and spread the word. If you have a large audience, you may even be able to hold your own conference or mastermind session.

I have personally had success being a speaker for companies around the world from Microsoft to Nextiva to Canon and more, focusing on sharing aspects of my business expertise. And, I have used my media commentating experience to become a sought-after interviewer on the stage, having interviewed Richard Branson for Virgin Atlantic, Bank of America’s CEO Brian Moynihan on Capitol Hill, Dave & Buster’s CEO Stephen King for the American Gaming Association, dozens of financial services leaders and many others, as well.

2) Curated eBooks: A great way to extend your content and brand, add value to a company and even help other influencers is by curating eBooks for brands. What I have done for brands like Microsoft is find a topic that resonates with the audience they are trying to reach. I include my content and I hand pick other influencers (some paid, some who just want exposure), to contribute their content, as well.

After the company adds their own branding, you all promote it. The brand can distribute it to existing and prospective customers, and you and your participating influencers can promote it through social media and other mechanisms that you use to reach your own audience. This not only can earn you a great fee, but it provides a tremendous amount of value to all participants, including other influencers who may return the favor one day.

3) Consulting: As an influencer, you are both an expert and someone with audience reach. That is very valuable to small and large brands alike who are trying to reach that audience. Whether they need feedback on future products, insights on the audience or other aspects of your expertise, offer half day and full day consulting rates. This is a way to monetize the good old fashion “picking your brain”, while adding value to your brand partners.

Often, these consulting gigs can extend to other monetization opportunities, such as speaking or content creation, so don’t forget to invest in the relationships that you create with companies on an ongoing basis!

4) Branded Products and Services: While many influencers spend a lot of time promoting the products and services of other companies, a small percentage have taken the time to create their own product offerings. I have done this successfully with offerings from my book, The Entrepreneur Equation, to one-on-one consulting sessions and services, to my latest product, a legacy & wishes planning system called Future File.

Creating your own product or service gives you more control over marketing and income, and can have a lot of longevity. Pick something that is authentic to you and to your audience. There are many companies you can partner with for everything from product creation to fulfillment, if those tasks are not your forte.

This is also why I suggest that every influencer try to cultivate an email or text list. While it’s great to be Instagram famous or a LinkedIn superstar, having the permission to talk to your audience on your own schedule is the ultimate tool for influencers. I have done this over the years and slowly built up to a five-figure list that I have permission to email directly.

5) Joining an Influencer Platform: I suggest that to expose your brand and content ideas to a wider array of brands, you should join an influencer platform like Tinysponsor, an open sponsorship marketplace that helps brands to set appropriate marketing goals and success metrics and then, match them at scale with the relevant creators to create custom, engaging content on targeted platforms, ranging from social media to traditional media, events, venues, display spaces or any other types of creative placements. For disclosure, I am an investor in Tinysponsor, because I believe in the offering and the value it adds to brands and influencers alike.

What’s great about being part of a platform like Tinysponsor is that you, as a creator, get to set the type of content creation that you like to do and your pricing for it up front. Brands browse that and select your pre-set content packages or connect with you if they want something custom. I find this to be very effective, as often, brands don’t really know what they want from influencers, so it’s easier for them to “shop” for something that they like! And, it saves you time as an influencer from filling out repetitive and time-consuming RFPs.

Remember, with all of these- and any of the other myriad monetization opportunities- to make them your own. Also, be sure to pick ideas that are consistent with your strengths. If you are afraid of speaking in front of groups, perhaps skip that and focus more on curating an eBook or video work instead.


Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this. 🙂

I’m so curious and greedy, I’d love to have lunch or breakfast with as many interesting people as possible. I am a very entrepreneurial and out-of-the-box thinker and a consummate connector and helper, so I know I would generate value for anyone who spent the time with me.

I’d say that if there were any business leaders who wanted to use or co-market Future File to their employees, customers or audiences, that would be at the top of my list.

And, if there’s anyone in entertainment who is looking for a kickass, clever and funny talk or game show host, that would be right up there, too.

Originally published at medium.com

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