Table of Experts: Money mindset mastery
Published by Austin Business Journal
[ARTICLE] Gay Gaddis Featured in Money Mindset Mastery
Confidence with money isn’t just about understanding finances. It’s about trusting your judgment, taking calculated risks and making decisions that support your long-term goals. Those themes were the focus of The Foundation for Better Business’s recent She Means Business event which featured headliner speakers including Jan Ryan, serial entrepreneur, venture- backed CEO, University of Texas at Austin lecturer on women’s entrepreneurship, and consultant with 3Hills Ventures, and Gay Gaddis, founder of T3 and author of “Cowgirl Power: How to Kick Ass in Business & Life.” The closing panel, “The Confident Money Leader: What Every Woman in Business Should Know“ featured Allison Kaylor-Flink, senior vice president at NFP; Madison Runyan, private banker and community leader at Frost Bank; Stacy Bouwman, financial advisor and certified financial planner at Edward Jones; and Dr. Jaleh Daie, partner at Aurora Equity. The conversation was moderated by Gay Gaddis. Audience members Annie Hardy, chief AI architect and futurist at Split Futures; Mary Joan Cunningham, founder of Mary Joan Cunningham Advisors; Nakevia Miller, CEO and fractional CMO of iN Possibiliti; and Melissa Wood, founder of Missyve.co, also joined the discussion during the Q&A.
Gay Gaddis: I started my business in my early 30s with a $16,000 IRA and no outside funding. So I bootstrapped it, and bootstrapping it really taught me that you have to know your money and be willing to talk about it.
Financial decisions, investments and even estate planning are conversations many people put off, but they’re too important to leave to chance. As your business grows, it’s especially important to surround yourself with the right advisors and recognize when it’s time to bring in new expertise.
Allison, you spent 25 years in rooms full of numbers, lawyers and financial professionals. What was the moment you stopped asking permission to be at the table and realized you belonged there?
Allison Kaylor-Flink: When I look back, there wasn’t one defining moment. It’s happened many times in my career.
One of the turning points came when I became the subject matter expert people relied on. I was traveling to Houston to help clients, and early on, I worked entirely around their schedule. They expected me to arrive first thing in the morning, which meant arranging childcare, getting my kids ready for school and catching an early flight.
But once I proved the value I brought, the conversation changed. I could say, “Here’s when I can be there. Schedule my meetings back to back because I need to catch the afternoon flight home.” We’d accomplish everything we needed to, closing four deals in a single trip.
I had earned the respect to set expectations because they knew the results I could deliver. That confidence eventually led me to open my own business, The 401(k) Concierge, which was acquired by NFP in 2014.
Gay Gaddis: Madison, you started your career as a kindergarten teacher before making the leap into banking. How did you transition from the classroom into a successful career in finance?
Madison Runyan: It does sound kind of crazy when you think about it. I spent five years teaching kindergarten, then transitioned into banking. After a year in personal banking and six months in private banking, I was ranked No. 6 in the state of Texas. When I look back, my success came down to two things: relationships and a willingness to learn.
As a teacher, I had to build trust with students, parents, administrators and other teachers. Well, you can see how that skill translates to banking. You’re sitting across the table from people, listening to their stories and helping them build a financial path forward. You’re pouring into them.
I think that service piece is what really stands out when you’re building relationships. For clients, are you writing notes or delivering flowers when they’re sick? Are you doing the little things that show you care? Are you going above and beyond to build trust? As women, our hearts are often one of our greatest strengths, so lean into that.
The second piece is learning. When I entered banking, I didn’t know everything, but I was determined to learn. I read, listened to podcasts and asked experienced bankers to meet for coffee. I’d say, “Tell me how you handled that client conversation because I want to learn from you.”
So those are the two themes for me: relationships and learning. You build competence and then you get that confidence.
Gay Gaddis: Stacy, you spent 15 years in the nonprofit world before transitioning into financial planning. Looking back, what prepared you to take that leap into managing other people’s money?
Stacy Bouwman: It was a leap, and to be completely honest, I didn’t think I belonged in the financial planning world. At all.
After spending 15 years in the nonprofit sector, I was laid off and trying to figure out what came next. My father, who was a financial advisor, had been encouraging me to join the profession for years. Finally, he asked, “Why will you not consider it?”
I told him, “I have no idea what you actually do, Dad!”
He said, “Kid,” — and by the way, I was 46 years old — “Kid, I help people sleep at night and buy a gallon of milk without worrying about what’s in their checking account.”
That completely changed my perspective. I went home immediately after that conversation and searched for the top traits of a great financial advisor. The first was empathy. The second was building trust. Another was being a natural educator. As I read through the list, I realized I already had skills to bring to the game. What I lacked was the technical knowledge, and I knew I could learn that.
Like we’ve already talked about, I leaned on mentors, built strong mentor-mentee relationships and learned everything I could. I’m naturally a bit of a data nerd, so I enjoyed developing that expertise.
The other thing I realized was that I needed to become the rainmaker. I wanted to be the one creating opportunities instead of waiting for them. Once I understood that, I stopped worrying about whether I belonged and started focusing on the value I could bring.
Gay Gaddis: Jaleh, you built your career in academia, leading departments and advising presidents before becoming an entrepreneur. How did you go from being an established expert in one field to pitching your first venture and building confidence in an entirely new arena?
Dr. Jaleh Daie: Moving from academia to venture capital is one of the most radical shifts you can make. Academia — especially with tenure — means lifetime job security, the lowest possible risk position. Meanwhile, venture capital is the highest risk profile, meaning that 80% of your deals are going to falter or fail.
I’d spent more than 20 years in academia, served as a department chair and worked for the White House. I had tons of grant money, lots of graduate students, a lab full of people doing great research, but I had gotten to a point in my career where I wasn’t happy. I realized academia had become too political. I wanted to focus on research and education, but I found myself increasingly frustrated by the politics of academia. I knew it was time for a new challenge.
Before entering venture capital, I spent time at the David and Lucile Packard Foundation, where I led its science and technology division. That experience helped bridge the transition, and it confirmed that I didn’t want to return to academia.
When I began looking at venture capital, I asked myself a simple question: Which of my skills transfer? I realized I already knew how to evaluate technology because I’m a life scientist. I knew how to assess people because I’d spent years hiring, mentoring and leading teams. The only area where I felt less prepared was the financial side of venture capital. While I’d managed budgets as a university administrator and at the Packard Foundation, I didn’t have the deep expertise that many venture capitalists develop through an MBA.
Rather than spending years earning another degree, I decided to teach myself. I took courses, asked experienced investors to walk me through deals and learned on the job. That experience taught me that career changes are often less about starting over than recognizing how much of what you’ve already learned can transfer into a new field.
Gay Gaddis: Jaleh’s story highlights something important: the need to be willing to reinvent yourself. It can be risky to leave a comfortable position and step into something new, but sometimes those risks can be invigorating and lead to opportunities you never imagined.
When you look at your skills and experiences, you may find you have more to offer than you realize. Often, it’s not about starting over; it’s about recognizing how your existing strengths can translate into a new opportunity.
Stacy, you build trust with clients by understanding what they truly want and need. When a client undervalues themselves, what conversations do you have to help them recognize their own value?
Stacy Bouwman: This is such a good question because, honestly, it’s rare that someone walks into my office and is truly undervaluing themselves. What is usually happening is that they are overwhelmed.
My job is to help them work through that overwhelm. As women, especially as business owners or leaders in corporate roles, we often have so many competing priorities. We’re managing careers, families, aging parents and all the complexities that come with life. We’re trying to figure out how everything fits together.
So the first question I ask is, “What do you want your money to be doing for you in your life? What is important to you?” Then I ask, “What does success look like if you give yourself permission to define it?”
I think that’s a powerful question because, as women, we don’t always give ourselves permission to define success for ourselves. Sometimes we let other people decide what success should look like.
For one person, success might mean retiring at 55 instead of 65. For someone else, it might mean building a business, creating flexibility or taking care of the people they love. My role is to help clients identify what matters most to them and then create a plan to get there.
Once we move past the noise and overwhelm, I often find that clients already have the answers. I’m there to guide them, help them make thoughtful decisions and help them understand that they’re making the right choices for themselves and the people they care about.
Gay Gaddis: Madison, in private banking, you’re often having conversations with business owners about credit lines, cash flow and growth financing. What is one thing business owners are afraid to ask their bank for but should be asking?
Madison Runyan: I think the biggest thing business owners are afraid to ask for is help. I recently read an article from SCORE that 80% of small business owners say the thing they wish they had done differently was ask for help sooner. They tried to figure everything out themselves, but it didn’t go right. By the time they reached out, the situation was much harder to solve.
I see that play out all the time. One business owner came to me early with an idea for a dessert shop. Because he came to me early, I was able to get a business banker in the boat and an SBA lender in the boat. We were able to bring everyone on board, and now he has clear steps in place to turn that idea into a business.
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