Skip to content

Female Founders: Tissa Richards On The Five Things You Need To Thrive and Succeed as a Woman Founder

An Interview With Candice Georgiadis

Leave the Work for Tomorrow. If you burn out raising money or running your company, you won’t be able to grow it to its full potential. If you never unplug, you’ll never succeed. As a founder, you could work 24/7/365 and never run out of important ways to fill that time. Here’s a secret: most deadlines and timelines are arbitrary. If you occasionally push them off until tomorrow to give yourself a chance to rest, the world won’t end. The work will still be there tomorrow, and so will your customers and partners. I worked nonstop for years, burning out and running on fumes. My best friend finally stole me away, treating me to a spa day and a weekend away with no laptops so we could catch up and rest. The work was still there when I got home. The company was still there. Customers hadn’t left. My team hadn’t quit in disgust. But I was refreshed and refocused. You will be too, and you’ll be ready to tackle the world.

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Tissa Richards.

Tissa Richards is a repeat Silicon Valley founder and CEO who has founded, funded and led software companies. Today she helps women unlock their leadership potential, eliminate imposter syndrome, and fearlessly communicate their value and leadership values to the world. Tissa keynotes frequently and her company holds corporate workshops and courses to optimize leadership teams and diversify c-suites and corporate boardrooms. Learn more at https://www.tissarichards.com

Thank you so much for doing this with us! 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’ve founded, funded and run software companies in Silicon Valley and beyond, secured multiple patents for complex cyber security products, and won awards for innovation from major Silicon Valley tech giants. That journey made me realize the importance of developing a generation of strong, fearless leaders free of imposter syndrome or self-doubt, and who communicate with confidence. After I wound down my last software company, I started a new company to help leaders and founders — especially women — become fearless and resilient by unlocking their leadership potential and their leadership values.

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

Running a startup company can be grueling, exhausting, and stressful. If you don’t take the time to refill your cup and rejuvenate, it will take a serious toll. (That’s one of the reasons I was so thrilled to participate in this interview!) There was a point during my last software company that I was struggling to make major financial and legal decisions that impacted the company, the team, the board, and myself. I was working around the clock, traveling domestically and internationally, and I was beyond burned out.

I started experiencing an unexpected phenomenon: my physical and emotional exhaustion was leaking out of my body in the form of involuntary tears. I began crying at random times and places without a precipitating event, many times without realizing it. Tears slid down my face in airports, airline lounges, planes, hotel lobbies, in green rooms before conference speeches, or in customer meeting rooms. I was usually unaware of it until people pointed it out! (Sidenote: This is a major signal that you are not thriving as a founder/CEO.)

An interesting upside of this phenomenon was how much human connection it sparked. Strangers rushed up to ask if I was ok, brought me tissues or chocolates, offered unsolicited but much appreciated hugs, and shared earnest suggestions on how to rest and rejuvenate. The most enduring connection was a woman I sat next to on a flight back home after a very stressful business trip. She passed me tissues as we bonded for the entire flight. We’ve stayed in close touch ever since and I was recently a guest at her daughter’s wedding! Leadership burnout shouldn’t happen, but I couldn’t have predicted the enduring friendships that would grow out of the deeply empathetic, human responses to it.

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?

When I started my last software company, I joined four prospective investors for dinner at a fancy steakhouse. They were all older gentlemen with impeccable Southern manners. About an hour into the meal, I stood up and excused myself to go to the restroom. I was pleased when they all stood up as well. I blurted out how glad I was that we’d all be going to the restroom simultaneously and could hit “pause” on our investment meeting. All four of them laughed good naturedly and explained that their Southern manners compelled them to stand up when a woman stood up. I had never encountered that degree of chivalry before. (I knew it was a real “Southern rule” when they all stood back up in unison when I returned — solo — from the restroom.) We had a good laugh at my confusion and continued the meeting.

My mistake was disarming and it broke the ice for the rest of the dinner. I didn’t try to be sophisticated or pretend it didn’t happen. I said what I was thinking and everyone appreciated it. It didn’t diminish me in anyone’s eyes. Several of them are cherished advisors and mentors to this day, and my gaffe has become lore with them. The lesson is clear: show up prepared, smart, and focused. Be yourself. If you’re genuine and authentic, you don’t need to be embarrassed when embarrassing things (inevitably) happen. Find the humor in the situation and move on. It won’t damage your credibility and you might get an enduring story out of it.

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’m sure we all remember how difficult and formative the middle school and high school years are. Everyone is trying to figure out how to fit in or else face the social consequences like teasing, bullying, or ostracism. I definitely didn’t fit in. I was smart, not socially “cool,” participated in multiple school bands and academic clubs, and I attended a gifted program one day a week at the local high school. That program changed my life.

The program founder and teacher, Mr. James Albery, showed his students that it’s not just ok to be different, it’s vital. He taught us that reaching your true potential requires accepting your uniqueness. In Mr. Albery’s program, my peers embraced my intelligence and sense of humor. I stood out, and not for the wrong reasons. I thrived. Those Thursdays in the high school had a lasting impact. They helped me realize the importance of being myself. The right people will recognize, nurture, and appreciate you for who you are. That message is a big part of my platform today.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

I believe there are two primary factors behind it: fear of failure, and a lack of sponsorship.

Many women experience fear. They fear they aren’t enough. They fear what people will think. They fear they don’t have the right skills or experience. That all rolls up to a fear of failure. What’s important to realize is that you’ll never have the exact right set of tools in your toolbox. We all learn as we go. And, it’s important to realize that failure is not fatal. Of course, failure is a possibility. In fact, most startup companies fail. But there’s always a next chapter and things to learn. It’s important to reframe failure. It’s not qualitative, it’s quantitative: it’s not that your foot is ugly, it’s that the shoe simply doesn’t fit your foot. That perspective help removes the emotion from failure. You are enough and you bring enough to the table. If you fail, it’s not the end of the world. It’s time to pivot and figure out what to do with the lessons you’ve learned.

The second thing is sponsorship. I want to draw a very clear distinction between mentorship and sponsorship. Mentorship is about providing advice and guidance, and it’s important. But sponsorship goes far beyond mentorship in very specific ways. Women who have been there before need to take responsibility and shepherd younger women towards success. Younger founders and leaders need to be able to call on sponsors for real questions. A friend recently told me about a young woman who bid on a contract with her company. This young woman underbid herself so significantly compared to other vendors that my friend was compelled to take her aside and show her how to price her services. We need to provide that kind of specific help to founders. For example, sponsors can point out holes or weaknesses in business plans, pressure test pricing models, or introduce attorneys they trust to review term sheets. Whatever the topic, founders need both general support and hands-on sponsorship.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

Schools and companies should invest in leadership programming to teach women from a young age how to identify, internalize and communicate the value they bring. That significantly reduces insecurity and fear. We should teach all young people how to handle failure and rejection so they approach opportunities with excitement instead of trepidation. And, mentorship programs should be formalized — and then honestly assessed — to make sure they aren’t in place just to check a box. I know firsthand that many large organizations have formalized mentorship initiatives that don’t provide much — if any — value to rising leaders. It’s a broken system, but it can be fixed.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

It’s challenging to be a founder. You are required to make high-impact decisions rapidly, in high-pressure, resource-constrained conditions. Hard conversations and sacrifices are part of your daily life. You must be persuasive and articulate. You have to be simultaneously realistic, optimistic, and a big-picture thinker. You need to have a detailed grasp on all the moving pieces of the business plan and P&L, and understand the big trends of technology, innovations, and the market.

That all demands consistent leadership and a thoughtful response to challenges. It requires integrity and an intentional set of leadership values. As a founder, you need to do the right thing, even when it’s difficult or costly to do so. Even more critically, you must model that kind of leadership to your company. Your leadership DNA becomes the company’s DNA, setting the tone for everyone else. We need more founders with clear values and integrity who make consistently principled decisions, whether male or female.

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

I’ve love to dispel five myths.

Myth 1: This an Easy Way To Make Tons of Money

Reality: Being a founder can be grueling. Raising money is hard. It can be lonely. There’s a high failure rate. Very few companies turn out to be unicorns and very few founders turn out to be the next Mark Zuckerberg. That doesn’t mean you shouldn’t go for it, but you need to be realistic. There’s a good chance you won’t make hundreds of millions of dollars. There’s also a 100% chance you will learn a ton, and there will be many enjoyable (if not glamorous) parts of the journey.

Myth 2: You Succeed by Hustling

Reality: There’s an unfortunate cultural allure and badge of honor for founders to brag about how hard they work or how little they sleep. You’ll have cycles of chaos and intensity, but those are not sustainable for the long term. If you burn out, you won’t be there to nurture, grow and scale your team and company. When you thrive, your company thrives.

Myth 3: The Ends Justify the Means

Reality: Don’t make a deal with the devil in order to succeed, no matter what the deal is, or who the devil is. It will come back to bite you. Make a commitment to your integrity. Do everything the right way from Day 1. Treat all your stakeholders with respect. If you find yourself in a situation where someone at the table isn’t committed to their integrity, don’t be afraid to get up and walk away. You may lose that hand, but you will come out ahead in the long run.

Myth 4: All Money Is Created Equal

Reality: Many founders believe it’s more important to raise money than to raise the right money. Your investors bring far more to the table than “just” financial capital. Your relationship with your investors is also about the network they introduce you to, the way they conduct business, and the culture you’re establishing for your company. Ultimately, this relationship will impact your resilience and how you thrive as a founder. Be as selective about choosing your investors as they are in making their investments.

Myth 5: It’s More Difficult To Be a Female Founder

Reality: It’s hard to be a founder, period. The more you focus on what’s hard about being a woman, the more challenging you’ll make it for yourself and your company. Focus on identifying mentors, sponsors, a support network, your core value, and your key operating values and integrity. Strengthen your financial and business acumen and your leadership and communication skills. Learn, improve, and thrive.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

There are 7 key traits that impact success.

  1. Successful founders navigate the emotional ups and downs. You experience the highest highs and the lowest lows in the same day. Some days you experience them in the same hour. You may even experience them in a single meeting. This is more like emotional whiplash than an emotional rollercoaster. You need to handle this with resilience and grace.
  2. Successful founders handle the loneliness. This will be one of the most intensely lonely and private experiences of your life. You have to present an energetic, positive face to your team and to the world, even if you’re tired or worn out, and the road ahead of you seems long.
  3. Successful founders delay gratification. The fruits of your labor may not be apparent or recognized for months — sometimes years — yet you have to stay focused on the end goal while working extremely hard for a long time.
  4. Successful founders are persuasive. You need to bring a wide variety of people along on this journey with you. Your vision of the product, the value proposition and the market value have to be incredibly compelling to convince investors, customers, partners, and your team to take a risk.
  5. Successful founders ask for help. You need to recognize and communicate your strengths and weaknesses to bring on board advisors and mentors who can help accelerate your path to success.
  6. Successful founders take accountability. You have the privilege of sharing successes with your team, and the burden of taking personal responsibility for the actions of that team. It falls to you as the founder to take the accountability for failure even if it is not directly “yours.”
  7. Successful founders are genuine, empathetic listeners. Being an effective founder is only possible when you listen deeply to your stakeholders, especially those who you ask to take risks with and on you.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Woman Founder?” (Please share a story or example for each.)

  1. Failure Is Not Defeat. This distinction is critical to thriving. Failure simply means the lack of immediate success. Defeat is feeling overwhelmed and demoralized by adversity. Remember, failure happens all the time. Sometimes it’s impacted by external factors out of your control, like long customer sales cycles, pandemics, or global supply chain crises. Other times it’s impacted by internal factors like decisions that felt right at the time, or intuitions you followed or ignored. As long as you can distinguish between failure and defeat, you’re on the right track. Refocus and make alterations to your strategy. Learn from your failures. You’ll make progress, grow, and develop resilience. You’ll thrive no matter what successes — or failures — come your way. I speak publicly and honestly about the failure of my last company in front of thousands of people each year, turning the lessons into a thought leadership platform for my new company. I’ve turned that failure into my biggest success.
  2. Know What You Bring to the Table. If you don’t know the answer to “who are you” or “why you,” a dangerous vacuum forms. All sorts of things rush to fill vacuums, including self-doubt, worry, imposter syndrome, and power imbalances. No one is going to give you the answer to the questions, so take the time to figure out exactly who you are and what you bring to the table. This helps you develop an unshakeable sense of self. Women who have taken the time to do this work have increased their compensation by 2.5X, secured stretch roles, and found the confidence to leave amazing jobs to follow their passions and start their own companies. Knowing your value also helps when you’re in a difficult situation or feel thrown off balance, enabling you to remain calm and focused. You’ll bring the best of yourself at all times, maximize your potential, and thrive.
  3. Know Your Non-Negotiables. As a founder and leader, you’ll encounter situations that require you to make difficult decisions and advocate for yourself and your team. Know ahead of time what your operating principles and values are, and what you won’t give up at any cost. Living every day with this north star gives you a solid footing to operate on. You’ll never be taken by surprise in a challenging situation. You won’t have to guess how you’ll react or what you’ll say. One of my non-negotiables is not accepting yelling or bullying behavior in my companies. When it happens, I calmly stand up and explain why I’m pausing the situation until everyone calms down or behaves differently. I’m not flustered, apologetic or defensive. Knowing your non-negotiables gives you courage, energy, and resiliency so you can grow your business and reputation, and leave a thriving leadership legacy.
  4. You Don’t Need Permission. You’ll thrive and be successful if you’re authentic, and you don’t need anyone’s permission to be your authentic self. People invest in you as a founder, choose to work with you and for you, and trust your leadership every single day. When you are authentically, unapologetically yourself, people know how you are likely to respond and react in any situation. This provides the consistency and reliability necessary for effective leadership. As a software CEO, my engineers knew exactly how I’d react. When they approached me with an audacious suggestion to port our software to a new operating system — a lengthy, costly endeavor — they knew I’d listen respectfully and calmly and make a reasoned decision. It turned out to be the right choice for the company. When you lead authentically, you don’t use up energy being anyone else. You preserve your resilience to grow your company, so everyone succeeds and thrives.
  5. Leave the Work for Tomorrow. If you burn out raising money or running your company, you won’t be able to grow it to its full potential. If you never unplug, you’ll never succeed. As a founder, you could work 24/7/365 and never run out of important ways to fill that time. Here’s a secret: most deadlines and timelines are arbitrary. If you occasionally push them off until tomorrow to give yourself a chance to rest, the world won’t end. The work will still be there tomorrow, and so will your customers and partners. I worked nonstop for years, burning out and running on fumes. My best friend finally stole me away, treating me to a spa day and a weekend away with no laptops so we could catch up and rest. The work was still there when I got home. The company was still there. Customers hadn’t left. My team hadn’t quit in disgust. But I was refreshed and refocused. You will be too, and you’ll be ready to tackle the world.

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

I hope I’ve used my success to make the world a little bit better by modeling and living my core message. Unlock your leadership. Live your values every single day. Be unapologetic and fearless about them. Never compromise your integrity. It’s incredible to hear how this message has led to life changing moments for women. They deescalate conflict or have uncomfortable conversations by calmly describing how they operate in the world and why they operate that way. They find the confidence to negotiate large salary increases or secure “stretch” or dream roles by clearly explaining the value they bring. They find the courage to leave amazing jobs and companies to follow their passions and — finally — feel fulfilled. The rush of joy and amazement I experience every time I hear this is so fulfilling.

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’m honored to be considered a person of great influence. A dream movement would be if more organizations — schools, civic organizations, sports leagues, companies — asked members, “who are you, who are you as a leader, and who are you in your life?” That helps people do some really important self-discovery work. Imagine what that could unlock in leadership, in society, and in the world.

If we made the time and space to answer these questions, we’d know a lot more about ourselves and about each other. We’d have more confidence, communication, and civility. We’d know how to interact in the most effective way to get things done. We’d know how to optimize potential, from the youngest child to the most senior leader of a global F50 organization. If everyone could instantly tell you how they operate in the world and why — and listen to and respect each other’s answers — we’d create a lot more space to empathize and be effective.

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.

Brene Brown, Arianna Huffington

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

Female Founders: Tissa Richards On The Five Things You Need To Thrive and Succeed as a Woman… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.