Madeline Reeves of Fearless Foundry: Five Things I Wish Someone Told Me Before I Became A CEO

An Interview With Doug Noll

Get it in writing — As nice as someone might seem on a call, anytime you decide to go into any form of business with someone, ensure there is a proper contract in place outlining the details of that agreement, and if any money is exchanging hands, how that process will take place.

As a part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Madeline Reeves of Fearless Foundry.

Madeline Reeves is the Founder and CEO of Fearless Foundry, a creative consultancy that supports ambitious founders from seed to scale through go to market strategy, content marketing, and design work. She has spent her career serving as a business development leader working for technology companies ranging from small startups to large publicly traded companies. She launched Fearless Foundry in 2017 to help business leaders boost their branding and internal strategies to build better businesses and work with clients they love. In addition to her roles as a CEO, founder, and coach, Madeline also hosts the Finding Fearless and Creative Friction podcasts.

Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I started my career in the world of internet technology, working in business development groups for scaling software companies, but rose quickly through my corporate career, and ended up leading an international tech startup. During my time in technology, I started to recognize all the ways in which underrepresented founders didn’t have the ability to scale their companies because of a lack of resources. I started to get a lot of inquiries from folks that knew my work about consulting with them on launching a company of their own. I began to support a select set of founders when I wasn’t working my day job by offering consulting, branding, and digital marketing support. I quickly realized that the need in that sector was massive. After about two years of working on those sorts of projects on the side, I decided to set up a shop of my own to focus on helping underrepresented founders through branding, marketing, and strategy based services.

Can you share the most interesting story that happened to you since you began leading your company?

I’ll tell a relatable story — and hopefully it is interesting too. About 12 months into working on Fearless Foundry full-time, I hit a huge wall, which most solo founders do. It was the result of major burnout. As fun as it was to be my own boss and not have the limitations of other people’s expectations or ideas on how I should be running the company, it ran me down. I’m a super ambitious person, so I was just working all day, every day to try and make sure my company was successful. I had more ideas than I could execute on my own. During that big bout of burnout, I was lucky enough to reach out to a friend who was also a founder, who strongly recommended I start building a team. Very quickly after that moment, my company grew to a team of 10+ employees, and nearly a million dollars worth of revenue. I realized I could go further, faster by bringing other people into the room. That’s probably one of the things I’m most proud of, the way the company grew when I created the opportunity for employment for other people.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

In the early days of the company, I was asked to consult with a very large accounting practice, because I had a background and a connection to the accounting industry from my previous career. They asked me to come in and support them with guidance as they implemented a new piece of technology for their team, as well as support regarding the strategy to start implementing it inside their services. I built everything, delivered the training presentation, got tons of praise and positive feedback for my work, sent my invoice, and then I never heard from them again. The funny or ironic thing about it is they were one of the largest accounting firms in the country. They had actually been a client of my previous employer. The big lesson I learned from that is: don’t ever do anything without payment details on file. That is the only way I now work with clients is by ensuring we have a deposit in place for the services that are going to be rendered and payment details on file.

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?

I am deeply grateful to the coaches and mentors who I’ve worked with along the way in terms of building my business, and particularly to my first business coach, Ivy Slater. Ivy was the first person to help guide me on how to negotiate sizable client contracts, which was a big struggle area for me early on in the business. It’s kind of ironic now, because I teach and talk so much about the importance of owning your value, and the worth of your work. It was a major change for me to go from negotiating six and seven figure deals for someone else’s company to then turn around and sell my services at that price point. I needed a lot of guidance and built a lot of confidence through working with her to understand the right ways to structure my coaching and consulting contracts. She taught me how to structure those contracts in a way that wasn’t undercutting the value of my work, but also was ensuring I was going to have great client projects and client relationships to go along with that.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?

I have had many situations along the path of scaling a team where I have had to decide the difference between what is best for individuals inside the company versus what is best for the team as a whole. In 2022, due to the unexpected loss of a quarter million dollar contract, we didn’t have the recurring revenue to continue to sustain all of our employees. As hard as it was to go through the process of laying off team members, it also led me down the important path of really evaluating who really made sense for the culture and the company that we were aiming to become, as well as who was really committed to our company’s shared values. Overall, as hard as it was to go through that process, as a leader who was having to rescind employment offers and cut roles, it was ultimately the right thing to do. I feel like it made both me and the company stronger.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

An executive bears the strategic responsibility of determining the vision and the path to execution for the company. For many of us, especially if we’re also the founder of the company, this means our brain is our business and our business is our brain. We are constantly thinking and working on how to improve the company. It can be challenging because it means our minds have to be three to six months in the future, despite the fact that our team or our clients might also need us to be able to be operating entirely in the present. We have to find this balance of vision and strategy based thinking to really set the course for the company. Simultaneously, you are responsible for making the right moves to ensure your team heads toward those desired outcomes.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

I think there’s a massive myth that’s perpetuated by social media that a successful CEO just runs their business from the beach. Although I enjoy taking vacations, I have yet to take one where I haven’t had to attend to the wellbeing of my company. That’s not because I don’t have healthy boundaries between myself and my business, but rather because in an early stage company with a small team, leadership requires a certain level of presence and diligence. That is why I really abhor the CEO mythology that’s out there that spreads the myth of, “Scale to seven figures! And then sail off into the sunset!” I think great companies require a level of intention and engagement from their CEO in order to really be successful. The reality is, running a business isn’t just life at the beach.

What is the most striking difference between your actual job and how you thought the job would be?

I thought I would get to a point pretty quickly where I wouldn’t be involved in client services. I have actually found that it is essential, in order for me to be aware of the underlying product or services that we sell, to continue to have a hand in the rendering of those offerings to our clients. I think I also thought there would be a time where I was just solely working with management and executive level leadership. However, I have a company that’s intentionally a certain size, and as a result, I am connected to all of my team members and talk to all of them throughout the course of the week. So far, I am yet to spend a week solely inside my executive level bubble.

Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

I do not believe everyone is cut out to be an executive. It takes a level of risk tolerance, and an ability to handle the hardest and potentially most stressful situations inside of a company. Executives shoulder the responsibility of making those decisions and handling potential conflicts. People who don’t have that level of tolerance for things like risks, conflict, and negotiation, whilst maintaining a positive vision, aren’t cut out to be an executive. To be an executive means you handle the hardest days, but still maintain a positive outlook for the future. So folks who tend to be really worried and get stuck in the weeds as opposed to seeing the big picture may not necessarily be aligned with the executive lifestyle.

What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?

I think it’s really critical to remember that cultures are built by people. The most important thing you can do to build a good culture is to pay close attention to the humans you hire. I’m a big believer in hiring slowly and firing quickly. It’s so important to be clear about the values behind your company in your hiring process to ensure the people you bring on board are already aligned with the values and intention behind the business you’re building. I also think, particularly if you run a company like mine where you have an entirely remote or almost entirely remote team, it’s super critical to create ways to build connections that extend beyond just collaborating on work projects. How can you integrate things like team retreats, happy hours, holidays, and gift giving into your company culture to create connections between people who don’t necessarily get the chance to work together in person? This is a question leaders of remote teams need to be asking.

How have you used your success to make the world a better place?

Through the work of my companies, I’ve created dozens of employment opportunities for individuals who either worked for or were contracted by my company. Additionally, we work almost exclusively with companies that have a level of social consciousness to them. Through elevating our clients and their branding/marketing, we give back to the world in a major way because our clients, in turn, care deeply about changing the world for the better. As I have continued to grow, my success, and my companies, I’ve worked really hard to build a business model that incorporates giving back as a core part of that offering. Over the past five years, I’ve mentored 100+ women at the intersection of entrepreneurship to help them build brands of their own and create their own financial success.

Fantastic. Here is the primary question of our interview. What are your “Five Things I Wish Someone Told Me Before I Became A CEO” and why? (Please share a story or example for each.)

1 . Get it in writing — As nice as someone might seem on a call, anytime you decide to go into any form of business with someone, ensure there is a proper contract in place outlining the details of that agreement, and if any money is exchanging hands, how that process will take place.

2 . Don’t do it without a deposit — In the world we live in right now, there’s a lot of people who are feeling scarce about money, but you shouldn’t have your cash flow affected by someone else’s poor financial decisions. So do not do any work ( especially large cost project work) without some deposit in place, and the client’s payment details on file.

3 . Hire other unicorns — When I became a CEO, I struggled with the idea that I wanted to have a team that was essentially clones of me. I wrestled a lot with whether or not that would be appropriate or detrimental because I’m a lot to handle. But ultimately, I started to recognize the way in which the clients I attracted were people who wanted to work with me or someone like me. Rather than settling for team members who were not committed to the mission or didn’t care about the work we were doing, I only hired people who held themselves to the same standards and quality that I hold myself to. This created a team of unicorns rather than me and a team of people who didn’t align with my mission.

4 . This job is a lot different than Instagram makes it look — Being a CEO requires you to carry the stress and liabilities that come with your company, as well as all of the risks that come with being in business. You need to put the right support systems around you in order to ensure you will have the wherewithal to manage that whilst maintaining your mental health. Get a coach, get a therapist, get a business shaman, get whatever you need to ensure you are supported so you can grow your company without having it harm your wellbeing.

5 . Trust your gut — There are so many things that condition women to override the intuitive abilities we have. Every time I have made some of my best choices or my worst, I have always had a gut instinct about it. The hardest things that have happened to me in business have happened when I didn’t listen to my gut. Therefore, it is critical that we do listen to ourselves, because our intuition is a key tool to utilize as a leader.

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

I started my company in order to generate capital to the point where I would be able to support emerging founders, and give back to them in a true monetary way. Founders, particularly underrepresented founders and female founders, are still under financed in comparison to their male and white counterparts. If I could change anything in the world of business and leave a legacy behind me, it would be to create better structures and institutions to pull resources and revenue together in order to fund the many, many overlooked ideas of brilliant underrepresented founders. Statistically last year, the amount of financial investment female founders received significantly decreased, and the same was true for founders of color. Also, statistically, those types of founders perform far better with investment dollars. So I believe there needs to be a huge shift in the world of venture capital and small business financing to ensure money is equitably placed in the hands of some of the most brilliant, and potentially viable, founders of our time.

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

“Let go of who you think you’re supposed to be to embrace who you are.” — Brene Brown

The lesson, for me, is that I had lots of thoughts and ideas of who I would be or become by being the CEO of my own company. Rather than holding on to one fixed idea of what it looks like, or what it means to be a CEO, it’s been a lot more satisfying to let go of that idea and allow myself to continue to evolve as a leader. I find more value in becoming whatever my company is needing in a particular time or season, as opposed to just holding on to a model that might no longer make sense for me when it comes to what it means to be a CEO.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

I think, lately, I am looking a lot at the story and wisdom of Serena Williams. I have been following, with rapt attention, her transition out of the world of sports and her rise as an entrepreneur and investor. It’s very clear she does all of those things with great levels of intention, in addition to being an icon and a mother. I find a lot of inspiration from individuals who have left one career and transitioned to another, and I would love to sit and chat with her. Specifically, I would love to pick her brain on what she does to maintain the efforts and energy she’s giving to her work while also pursuing the things she’s most passionate about.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

About the Interviewer: Douglas E. Noll, JD, MA was born nearly blind, crippled with club feet, partially deaf, and left-handed. He overcame all of these obstacles to become a successful civil trial lawyer. In 2000, he abandoned his law practice to become a peacemaker. His calling is to serve humanity, and he executes his calling at many levels. He is an award-winning author, teacher, and trainer. He is a highly experienced mediator. Doug’s work carries him from international work to helping people resolve deep interpersonal and ideological conflicts. Doug teaches his innovative de-escalation skill that calms any angry person in 90 seconds or less. With Laurel Kaufer, Doug founded Prison of Peace in 2009. The Prison of Peace project trains life and long terms incarcerated people to be powerful peacemakers and mediators. He has been deeply moved by inmates who have learned and applied deep, empathic listening skills, leadership skills, and problem-solving skills to reduce violence in their prison communities. Their dedication to learning, improving, and serving their communities motivates him to expand the principles of Prison of Peace so that every human wanting to learn the skills of peace may do so. Doug’s awards include California Lawyer Magazine Lawyer of the Year, Best Lawyers in America Lawyer of the Year, Purpose Prize Fellow, International Academy of Mediators Syd Leezak Award of Excellence, National Academy of Distinguished Neutrals Neutral of the Year. His four books have won a number of awards and commendations. Doug’s podcast, Listen With Leaders, is now accepting guests. Click on this link to learn more and apply.