“Focus” with Kristi Ross and Tyler Gallagher

Lose some money trading. Now that seems counter-intuitive. You will learn an incredible amount when you have your own money on the line. It is better to lose a small amount of money and learn from it when you’re younger than lose your retirement nest egg when you’re older and trading for the first time, […]

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Lose some money trading. Now that seems counter-intuitive. You will learn an incredible amount when you have your own money on the line. It is better to lose a small amount of money and learn from it when you’re younger than lose your retirement nest egg when you’re older and trading for the first time, or simply trading too big.

As a part of my series about strong female finance leaders, I had the pleasure of interviewing Kristi Ross, co-CEO and President of tastytrade. Kristi Ross is the co-CEO and President of tastytrade, the most-watched online financial network that strives to make finance fun and actionable. She is a co-Founder of a visual front-end trading technology platform launched in 2014, which later became a regulated, online brokerage firm called tastyworks in 2017, a FINRA, NFA, SIPC member. Ms. Ross serves on the board of tastytrade and is Chairman of tastyworks. The tastytrade and tastyworks collective focuses on empowering the do-it-yourself investor to engage more with their finances through the unique combination of content and technology. Ms. Ross also co-hosts the show Bootstrapping in America, where she interviews innovative entrepreneurs. Previously, Ms. Ross was the CFO of thinkorswim Group, as a private company, where she led numerous mergers, acquisitions and integrations. thinkorswim was sold to TD Ameritrade for $750M in 2009. Prior to thinkorswim, Ms. Ross was CFO of Automated Trading Desk Specialists, a stock specialist on the Chicago Stock Exchange. Ms. Ross started her career in public accounting, specializing in financial services industry clientele including individual traders, proprietary firms, market makers, specialists, discount brokerage and advisory firms. Ms. Ross has been a female vanguard in and around the trading industry for more than 25 years. As co-CEO and President of tastytrade, Ms. Ross has been honored as the Illinois Technology Association CityLights’ Prominent Tech Woman, the Moxie Awards’ Woman in Tech, Entrepreneur of the Year by Ernst & Young, James Haugh Award recipient and has been named to Innovate Finance’s Global Women in Fintech Powerlist, Crain’s Chicago’s Tech 50, the Techweek 100 list, Chicago Business Journal’s Women of Influence list and Midwest Women in Tech Award. Ms. Ross has spoken at Techweek, WiSTEM, Ms. Tech, Woman 2.0, and Chicago Ideas Week and has been featured by prominent publications such as Fortune, Chicago Tribune, and Crain’s Chicago. In addition, Ms. Ross is an active board member of companies in the banking, trading, technology and finance industry. She has been an active member of the ChicagoNEXT Fintech Council of World Business Chicago, P33 Technology Initiative, board member of CEC/1871, Economic Club of Chicago member, and The Chicago Network. Philanthropic passions include Midtown Educational Foundation, Rock the Street Wall Street, EveryHandCounts, entrepreneurship, financial literacy and the importance of physical fitness.

Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to the Banking/Finance field?

Noone really knows what they want to be when they grow up until they are truly exposed to it. Conversely, that exposure may also clarify what they don’t what to be. I knew that I loved math and was good at accounting, so I decided early on that I would try public accounting with the hope that I would be exposed to a variety of industries. That’s exactly what happened. I was lucky enough to experience the world of trading via Chicago’s vast trading community (CHX, CBOE, CBOT, CME) back when there were still trading pits with open outcry on physical trading floors. Today, less than 10% of trading is done on physical trading floors. The energy of the floor at the time and the volatility of the financial markets drew me in. As a certified public accountant (CPA), the clients I enjoyed working with the most were traders, proprietary trading firms, advisors and brokers. I knew the trading industry is ultimately where I belonged.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

When I was 25-years-old, working as a public accountant, one of our clients needed a CFO. What did I do? I raised my hand. To my surprise, I got the interview and the job! I ran out to a bookstore, back when Amazon didn’t exist, and bought a CFO handbook. I remember it so clearly, all the way down to the cover of the book which was a deep forest green. I also bought a CEO handbook to better understand what a CEO relied on, which would allow me to more succinctly provide the right information. That book was bold, basic black, and exactly what I needed. Looking back at the reason I raised my hand, it wasn’t that I thought I would be the best CFO ever at age 25; but rather, I raised my hand because I was confident I could figure it out. With hard work, focus and dedication, I believe you can do anything. Several studies show that most men apply for a job when they are only 60% qualified and most women apply for a job when they fulfill 100% of the qualifications.

My best piece of advice is to take risks. Be willing to raise your hand. Put yourself out there. Still hesitant? Ask yourself what is the worst that can happen. You will learn far more by doing and experiencing and putting yourself in challenging positions, than you will by taking a conservative, safe, traditional path. Learn to be comfortable being uncomfortable and you will grow and learn at an exponential rate.

Are you working on any exciting new projects now? How do you think that will help people?

I have been through over 30 mergers, acquisitions and capital raises in my career. I have been part of and have invested in several startups. We launched our current company, tastytrade, back in 2011. In eight short years, we’ve created seven companies and have more to come. We’re always working on new and exciting projects which create opportunities to help others gain financial and investing confidence.

Our mission of making finance fun, actionable and accessible has never changed. To give context of our newest ventures, I’d like to share what some of our companies do. With our parent company tastytrade, we deliver daily live shows to engage people in the financial markets. We then created technology to make complex concepts like trading stock, options and futures more digestible by making trading more visual. We also wanted to enhance the customer’s brokerage relationship and experience so we became a registered online brokerage firm, now called tastyworks. Then, we solicited the exchanges to make trading futures products more “retail friendly”. Self-directed investors should have the same opportunity to utilize the same types of products that institutional investors do. So, we decided to create our own exchange with smaller-sized futures products through the Small Exchange. We recently raised capital from some of the major players in the space, Citadel and Jump. One more exciting bit of news, is our new mobile investment app, Dough. We have created a team to curate the experience of engaging with the stock market to your mobile phone, with no commissions. While there are a lot of commission-free brokers out there, Dough’s differentiator is that they strive to provide people with ideas and insights into potential market opportunities. No lectures or jargon, but a creative team that produces innovative content that provides smart ideas for the market, while also offering commission-free trades.

We are able to deliver what the customers want, because we are customers ourselves.

What do you think makes your company stand out? Can you share a story?

We are unconventional, non-traditional and proud contrarians. We are traders that created a Fintech company where we all actively trade every day, no one reads from a TelePrompTer, and we feel the actual highs and lows as the market accommodates us and goes against us. My co-CEO, Tom Sosnoff, is a brilliant, trading veteran and serial entrepreneur. He has long hair and wears a beret. By nature, I am a strategic, risk-seeking, “accountant-at-heart” with an undeniable entrepreneurial core.

Our executive teams and on-air personalities have well over 300+ years of collective trading experience. We set ourselves apart from other financial services firms in many ways, but it all comes down to a culture of putting the customer first. We create an insane amount of free content (8 hours/day live original programming, consisting of over 50 different show segments, and hundreds of hours of research and probability-based analysis). While we do have educational content, the difference is that we show customers how to apply it in a real market environment, every day…it is that “learn by doing” concept. Our ecosystem of offerings, from our content to our intuitive trading technology, to our customer-centric online brokerage firm, we continue to innovate. Each additional offering stems from a need that the customer has or could have. Sounds simple, right? If you create the right culture, it is simple to always put the customer first. I feel like we’ve done that…every person treats every customer as if they are sitting right in front of them. We all answer customer emails directly, no matter what anyone’s title is, myself and Tom included. At the end of the day, the reason we are all here is to empower people to take control of their finances and ultimately gain financial confidence.

Wall Street and Finance used to be an “all white boys club”. This has changed a lot recently. In your opinion, what caused this change?

I am a firm believer that the male/female combination is far more powerful together than either on their own. Men and women are wired differently, and each brings an incredible amount to the table. As co-CEO’s, Tom Sosnoff and I challenge each other and we’re both better leaders because of it. We’ve built a culture where everyone has a voice…our employees, our customers, anyone who wants to make a difference. I would venture to say that we are not the norm. However, we are a good example of how it takes both sides to come to the table with an open mind.

Change is a two-way street, not only at our company, but industry-wide. There has been more awareness on the lack of diversity in financial services over the years. It starts with awareness, then accountability, and finally action. We have seen a mindset shift, that wasn’t there 30 years ago when I entered the field. It started as a boys’ club, I lived it. To get in, you needed to be invited in. What that means is someone, a male, needed to take a chance on you. But in order to get the chance, I needed to meet them where they were. I needed to talk the same language or at least be able to meld their language to mine and mine to theirs. I needed to be on the golf course where the deals were being done (thank God I was an athlete growing up and had a desire to learn to play golf). I needed to prove I could play on the same playground and earn their respect. It took a lot of extra effort, but I was determined. I learned that having a voice and having an opinion and sharing it made all the difference in the world. Being part of the conversation and adding value, made a difference. That’s where the two-way street comes in. Both sides could do more to shift the landscape and I believe we are starting to see that happen. We’re not there yet, but progress is being made.

Remarkably, online trading has leveled the playing field, because online trading knows no gender! Through the combination of easily accessible content and intuitive technology, gaining knowledge and experience in the field of trading is exponentially easier. Men authentically willing to open the club doors and women willing to walk through them confidently will need to be an effort that continues in order to effectuate real sustainable change.

Of course, despite the progress, we still have a lot more work to do to achieve parity. According to this report in CNBC, less than 17 percent of senior positions in investment banks are held by women. In your opinion or experience, what 3 things can be done by a) individuals b) companies and/or c) society to support this movement going forward?

I love this question, but I don’t love the current statistics. We all need to do more. While there are so many things that can be done to help foster future leaders in financial services, here are just a few:

a) Individuals: I am a firm believer that if you have a reasonable level of emotional intelligence, you can make a huge difference. To men: seek out a woman that you feel has potential and mentor her, invite her into the “boys’ club” as we know it in financial services. Help guide but also listen to the insights she has. Be open minded to different views. Women: go outside your comfort zone, take risks and be willing to come to the table, with an open-mind. Both genders should have the intention that it is about a meeting of the minds and teaching each other…a two-way street. This effort should be done at all levels. Then, once women can see other women in senior-level positions, it is easier to visualize themselves in that role. It won’t happen overnight. It needs to be a continuous effort.

b) Companies: Companies can show support for organizations like Rock the Street Wall Street. RTSWS is teaching and exposing girls in high school to financial literacy and the financial markets. Companies can help RTSWS fuel the future female leaders of financial services, not only through sponsorships, but also through encouraging their employees to be panelists, speakers, and mentors. Companies can also open their doors so the girls can tour their firms, and be exposed to what it is really like working in those firms. That single day could have a life changing effect on those girls and the choices they make.

c) Society: News outlets should continue to report diversity numbers to make companies accountable…it will lead to action. Society overall needs a shift, male/female responsibilities at home need to change. Women need to let the motherly guilt go and demand the sharing of responsibilities. Kids only know “normal” as their parents illustrate it. If partners respect the others’ career choices and consider each other equals, that is a good start. My example at home is a divide and conquer mentality. Equal sharing of the responsibilities, chores, schedules, meals and finances need to happen. Take a piece of paper, draw a line down the middle and divide the duties, equally. I’ll throw a strong suggestion over to my female counterparts to take the finance duty…bills, budgeting and investing or at least share in that responsibility. In my house, my rugby-loving, career-oriented, globe-trotting husband takes on chores equally. He does the dishes, is responsible for all insurance and car items, and a big part of the kids’ extracurricular schedules. I do laundry, the finances and investments and anything medical related. We currently share in meal prep and have an equal respect for the others’ career. It’s not perfect, but it certainly helps level the playing field, and sets a stellar example for my own three lovely daughters. When there is better balance at home, there is better opportunity for balance at work, no matter what industry you’re in.

You are a “finance insider”. If you had to advise your adult child about 5 non-intuitive things one should do to become more financially literate, what would you say? Can you please give a story or example for each.

  1. Create and be able to articulate your own financial story. Force yourself to create 10 personal key financial metrics. Start by memorizing them and then measure against them monthly or annually, just like you would do if you owned a company or ran a department. Examples could include: your credit score; total cash inflows vs. outflows each month; monthly entertainment spending; or a charitable donation barometer. You should know your top three expenses and their percentage of your overall monthly spend. Other metrics you could include: total assets vs. debt; your income tax bracket and annual taxable income; annual real estate taxes; amount saved or invested; number of investments and what the return on those investments generates. Satisfy your natural curiosity of why a number changed from one period to the next and dig deeper to find out. Then, create goals and benchmarks for yourself. No one cares more about your money than you do. Show it some love. It’s part of your story.
  2. Take risks. Create a mindset to step outside of your comfort zone. Most people are not comfortable talking about their finances, taking financial risks or making investments. If you learn to take small risks and small steps into something new, like investing, you will master it before you know it. A good example of that is trading. We talk about “trading small and trading often” to get comfortable maneuvering in the financial markets. Practice without putting a lot of money on the line.
  3. Lose some money trading. Now that seems counterintuitive. You will learn an incredible amount when you have your own money on the line. It is better to lose a small amount of money and learn from it when you’re younger than lose your retirement nest egg when you’re older and trading for the first time, or simply trading too big.
  4. Read. Read everything you can, written from all viewpoints so that you can identify the BS. There is a lot of financial news that is purely noise. No one knows what the financial markets will do. There are way too many factors that play into a stock’s price for anyone to know exactly what any stock will do. It is better to rely on probabilities vs. someone’s predictions.
  5. Teach someone something you want to learn about-a specific area of finance that interests you or better yet, scares you. I know, that sounds backwards, right? Utilize all the tools and information available, do a little bit of research, summarize it enough so that you can articulate the top three things about your financial topic so you can share it with someone else. You will be amazed at the trajectory of your learning curve in becoming financially literate.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

After graduating from college, I worked in public accounting. Our new-hire class had about 15 people in it. During orientation, a few different partners gave speeches about their areas of expertise. One partner gave a speech on networking, explaining that potential business is everywhere. You could be at a party, or on a plane, or at a baseball game…your antenna for new business should always be up. Your friends become your clients and clients become your friends. That speech was part of the foundation for a motto I live by: “opportunity is all around you, pay attention”.

I was lucky enough to be a part of his team at the firm. I worked hard and had the second highest billable hours in the firm. I later became dear friends with that partner and to this day look to him as one of the most impactful mentors I’ve had. He epitomized how men can play a role in lifting women up and helping them recognize opportunities that are right in front of them. I am forever grateful for the wisdom he bestowed, his graciousness inviting me into his network of people, his patience in teaching me what he knew and of course, I am grateful for his friendship.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I have a few life lesson quotes I swear by. My top quote is: “Opportunity is all around you, pay attention…but you have to grab it.” If you have your eyes and ears open, knowing anyone you meet could crack open the door to your success, you look and listen differently. Opportunity doesn’t just drop in your lap, you need to take action. You need to recognize it and be the one to make the first move to grab it. I learned early on in my career when I became a CFO at 25, that had I given in to the lingering doubts that many women in the workplace feel, I very well may have ended up with a different path. I truly believe having that CFO designation early on, springboarded me to my next CFO position with a stock specialist trading firm a few years later. Choices and risks you take today can shape better opportunities for your future.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger.

Happiness often stems from doing something you love, feeling that you have a purpose in the world, and feeling productive and balanced. It’s hard in today’s fast-paced, digital demand world to a find your “balance”. I gauge it for myself with my 5F’s:

● Finance

● Fitness/Food/(Ph)ysical

● Family/Friends/Fun

● Focus — -this often is your company or career, your passion

● (Ph)ilanthropy/Faith

FINANCE: I feel empowered simply by controlling my own finances. Numbers tell a story and if you realize you can control outcomes by the choices you make, you realize you are in control of your own story.

FITNESS: I’ve always been an athlete and all-around health conscious person, and I love running to stay in shape. For me, strong mental and physical health is the foundation for doing anything well. Making smart daily choices and keeping a routine helps build a healthy, strong lifestyle where you feel like you can conquer the world. Participating in things like the Chicago Wellness Challenge created by Pete Wilkins is a good way to get the word out about a healthy balance and keeping yourself accountable.

FAMILY: Family/friends/fun is another foundational pillar. If you feel happy and fulfilled at home, you can more easily tackle the hurdles at work. It’s not always a bed of roses, and I am someone who has to work hard at making sure I carve out time for the important relationships in my life. I am always grateful when I do, because I feel re-energized.

FOCUS: Finding the right industry or the right problem you want to solve is so exciting. It keeps you driven, creates purpose that you look forward to getting out of bed in the morning so that you can make a difference. The motto here is: “Do what you love, love what you do” so that it doesn’t feel like work. Strive to make a difference every day in some way. Strive to be a life-long learner and learn something new each day as well…and pass it on.

PHILANTHROPY: Find a way to give back. As a busy mom, I struggled when my kids were small to find a way to ensure that they were being exposed to philanthropic efforts. I looked for kids’ books on the subject and couldn’t find what I was looking for, so I wrote a children’s book called “Lots of Knots” about a young girl who cuts her hair and donates it to someone in need, teaching young kids that little hands can make a difference. I donate all the proceeds. It is the first in the series and I hope to come back to finish the other books I’ve started so that I can continue to make it easier for kids to connect with philanthropic efforts at a young age.

My 5F’s are all about helping others realize the power they have over their own happiness. And it starts with how they spend their time. Time is the most valuable resource we have. Once someone is making conscious choices, they start to realize it’s about accountability for their own happiness and “balance” in their life. True happiness and power starts with you…the choices you make, the opportunities you grab and the risks you’re willing to take. Grab that next opportunity and set out to change the world!

Thank you for all of these great insights!

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