Karen Mangia
On this Success from Anywhere blog, we'll get to know a serial Silicon Valley founder who turned failure into an opportunity to flourish. She's an author, leadership expert, keynote speaker, and coach to some of the world's largest private equity investment and technology firms, all while wearing her signature cowboy boots. This woman knows how to kick a little — Tissa Richards.
Karen Mangia
One question I ask everyone is: What was your first job and how did that job inform or inspire your career trajectory?
Tissa Richards
My first job ever was teaching piano to everybody from five-year-olds to my oldest student, who was 95 when she took her first piano lesson.
Karen Mangia
I taught piano as well. And I don't know about you; there is nothing like the joy of the moment when someone masters that first piece that's even slightly out of reach. It's such a joyous co-creation experience!
Tissa Richards
What's fun, too, is the joy of music. The most exciting thing was a kid running up my front walkway, bursting the door open, and saying, "Did you know that music is the same?" because I think he was learning flute or something in his band class. He said, “The music is the same. I don't have to relearn it. I have to learn how to play this instrument." And it was cute because he suddenly realized that all of music was accessible to him. That was an incredible day.
Karen Mangia
I said in the opening, you've got your signature cowboy boots. Tell us about that! How is that part of your superpower?
Tissa Richards
It's part of my brand. When I started my last company and moved from Silicon Valley to Austin, Texas, I realized I needed to improve at wearing high heels. You have to have some grace and coordination, and I have none. I realized that cowboy boots were comfortable to walk in for miles through airports and conference centers and things, and they come in really fun colors and patterns. I realized I could express myself and be comfortable in the process.
I'm all about finding your personal brand, not trying to fit in with what other people are wearing or doing, and being authentic. This was a way to be authentic and comfortable at the same time. So that's why I attend most meetings in a pair of loud but very comfortable cowboy boots. I like to tell people: show up, be you, and be comfortable. Don't try to don't try to put on a mask or fit in in a way that doesn't make sense.
Karen Mangia
Wise words from someone who is a founder. You mentioned the importance of finding your brand and being authentically yourself, which is core to your story of founder, failure, and flourishing. Take us inside starting a business. What happened, and what you've learned?
Tissa Richards
I've learned a lot. We've known each other for a number of years now; I have started a couple of companies. The last one failed spectacularly at the very end on the precipice of success. Then, for several reasons, we had to decide on a board and an executive team to shut it down to stay aligned with our values — to be true to what we knew was the right thing. And that cost everybody a lot of money and heartache— it was a difficult journey. I think that people fear failure; they think it's going to impact their reputation; it's going to impact their future chances at success. If you're doing the right thing, it will never impact you negatively as long as you don't conflate failure with defeat. Defeat is when you think that's it. I have personally failed. Failure is okay. If it didn't work, pivot, take the lessons, and do the next thing. I'm passionate about making sure that nobody is defeated by failure.
Karen Mangia
One of the differentiators is that defining moment in your story you referenced where you could have succeeded, and the reason you chose to close your business was a values mismatch. Say more about that because sometimes we assign a cost to our values, and we feel like the price is too high to pay, or sometimes the price is just right. Take us more inside of that story of what your values were. What was the mismatch, and how did you ultimately decide to walk away, realizing it would cost you everything except your integrity?
Tissa Richards
What if I can step back and make this a more global message, too? It's impossible to make those decisions because you are at the wheel. Things are happening so quickly; you must know what your values are. You also have to know what decision you will make at the moment. What's critical for leaders, for anybody at any stage in their career and life, is knowing your non-negotiables and why they're your non-negotiables. Those can be different for everybody. But to know, this is what I hold very, very close, these are my values, and this is why, and this is when I'm going to stand up and say, “No matter what this costs me, I am not going to budge on it.”
It can be anything—even as seemingly low stakes as respect, which is one of my non-negotiables. If a situation escalates, you won't get the best work out of me. So, I'm going to be able to say, let's put a pause on it and come back when we're all calmer because that's how I work the best. That can be a non-negotiable to the most extreme, which, in my case, is our org’s case. We can no longer take the terms given to us; we can no longer work within this environment that our investors or partners are getting us to; we must decide to pause the company. Knowing that in advance is key. Otherwise, when the stakes are high, and things are coming at you fast and furious, cognitively, it is challenging to have that clarity. Note going in: I always do these workshops where you go in and say, “I'm going to do this; this is a moment without high stakes, without tension. Here's what's important to me; here's why. Here's how I will make everything from the lowest to the highest stakes decision and contextualize it within my values.” That's key to knowing your non-negotiables.
Karen Mangia
Consider your non-negotiables and values when you're not under pressure and needing to rely on them as a filter for decision-making. That is a great tip. And also, know your why—not just what you value, but why you value that so much. You talked a moment ago about sitting between defeat and failure. People are reading and thinking you're crazy to walk away. You can find a great therapist or an executive coach who will help you through the values mismatch—take the money and keep going. On the other side, you must have entered some valley of despair. There's no way you were sitting around saying, "Good news, pop the champagne. I'm living in alignment with my values and doing great.” How do you get through that setback to comeback process?
Tissa Richards
Whether shutting down a company or leaving a job that doesn't feel right anymore, it's a process. You hit the nail on the head here. And, you know, when I did my TEDx talk with you a few months ago, it was about resilience being a muscle memory. The more that you do this, the more you're able to make those decisions based on your values. The more you'll be able to, number one, do it more automatically, but it does, ultimately, increase your resilience. That's not to say that immediately, to your point, you're going to pop up the next day and go, “Oh, I just gave notice, and that was really easy,” or, “I just shut down a company that cost me millions of dollars; that was fun.” It's not fun. But, as you come through it, process it, and realize what your other decision paths are, you could have done something that could be totally misaligned, which would be bad for your reputation. Ultimately, it will cause tension in the cognitive dissonance of doing something you know is wrong. Let's say you're in a role that is just not—it's a culture mismatch for you, where every day you come home, and you think, “I'm exhausted.” Work is tiring as it is, right? Giving it your all is tiring. If you're also in a place that's not right for you, it's increasingly tiring. So, the more that you're doing something that is not aligned with your values, and where you give the best value for yourself, ultimately you're not going to be resilient, you're not going to be the most effective, and it's just going to chip away at you.
When you come out of it, you decide to say, “I'm putting my foot down; this is a non-negotiable; I'm going to step away.” It's hard; it may make you feel like you failed. It may make you feel like this was a hard decision. But the more distance you get from it, especially when contextualizing that decision, the more you'll get through. It might cost you some money. You might feel embarrassed, but the narrative is a good one. And you'll get through it. I promise. It is always a comeback if you've decided for the right reasons.
Karen Mangia
You wrote a book called No Permission Needed, and you take people through the process of defining your values and thinking about who you are as a leader. One of the powerful statements in the book is: your values are a fact. This isn't anyone's opinion; they are a fact. What other wisdom would you offer people thinking about what kind of leader they need to be now, given the context shifts we've all lived through in the past couple of years and certainly more to come?
Tissa Richards
It's really important, and I am so glad you reminded me of that because the corollary to that is that your value is a fact. So, your values are a fact and the value you bring is a fact. One of the things that so many people say to me is that it feels arrogant to say, “Hey, this is what I'm known for. I'm known for creating these outcomes. I'm also known for creating those outcomes by leading teams with this leadership style or with these values.” Being able to say that out loud and always connect it to outcomes is essential, especially as you want to get through your career, as you want to accelerate, as you want to get your team motivated. Setting context is critical that way.
This is why I get frustrated when someone comes up to me and says, “Hey, my superpower is empathy.” Okay, I'm slightly underwhelmed by that unless you can tell me why that matters. If you can say to me that empathy is a superpower because it makes everybody feel valued, it creates psychological safety, it makes people think that they can experiment and be safe doing that—what you've done is connect that directly to an outcome at an individual level, a team level, or even an organizational level. Now I understand the ‘so what’ of that. If we can learn how to think that way, speak that way, and communicate it to each other and anyone that matters, I think we've given this ‘so what’ of those values.
Karen Mangia
What showed up for me in what you just said is that values are something that you define and hold close to yourself so you are in a position to deliver value to other people and never confuse the two. Values are for you to show up at your best. Value is linked to the outcomes that you create as an extension of that for others. Let's talk about shifting focus and how you're spending more time talking with everyone—from founders to funders to board members—about this concept of outcomes. Say more about the coaching you provide on that topic and why that matters to all of us.
Tissa Richards
So much of what I do is always connected to the outcome. The question I ask every day, and I say it with love, but I say it straightforwardly, is: So what? So, when somebody comes and says, “Here's who I am, here's what I do,” I'll always say, “So what? Tell me why that matters.”
And that's how we make companies memorable. That's how we create company brands. That's how we create personal brands. The most important thing about connecting what you do with why it matters is anchoring you in people's minds and reducing team friction; anything we do is the ‘so what’. Right? When you talk about yourself, you must clarify why what you do matters. Why does your work matter? How do you create an outcome? How do you motivate your team?
The most important question is: So what? If we have a new revenue target, if we have a new set of KPIs—so what? What is our new strategy going to be to get there—so what? When we can get super clear on that, everybody is suddenly working together. And if you're going to say, “The way I work is this way.” So what? How will that connect the outcome, people, and work? It's the glue, but many people need to improve about being specific. So, what are the specifics? That's how we build the skills to get there. It's the practical, the tangible, the actionable. How are we going to get there? What do we need to do to close the gap? And a lot of people need to improve at answering this ‘so what’?
Karen Mangia
And you're an advocate for ‘so what’ as a tool for developing and sustaining psychological safety; say more about that.
Tissa Richards
Yeah, it's also about self-advocacy. If you can say, for example, “So what—here's why what I do matters.” That's also a way of saying why you should be able to, for example, get that new title, get this compensation, be a part of this team.
Or, if you can be clear about the goal of an organization or a team, your leaders will give you much more space as a team to go and work that way. They will not micromanage you; they will provide you the freedom and the flexibility to work towards that outcome. I'll give you an example. When I was a CEO, my team knew they could do what they needed as long as we were working towards the outcome. They told me we should put our whole product into a new operating system. I'm glad I was sitting down because that is a big undertaking. That's different from saying we should be on iOS instead of Android. It was the entire company—basically everything we had created to date, four or five years of coding—but they had been tinkering in the lab and saw our pipeline. They saw our product roadmap and said where we are, which was on Linux, will probably not get us where we need to go. We should go over to FreeBSD, which will be more robust. We won't fall over; we'll be able to scale the way bigger networks more securely. And I said, “Well, tell me what that means. We're going to be six to nine months behind on our deliverables.” So, I had to go to investors, I had to go to customers, I had to go to partners and say, “That significantly impacts our capital roadmap, our product roadmap, our deliverables, but the team feels that this is why we should do it. And here's what it means.” But my team felt safe; they felt safe coming and saying, “We've done some tinkering and experimentation.” Everybody was safe doing that, but they also knew what the so what was—we wanted a great valuation for the company; we wanted to get to things. This wasn't just two months in the roadmap; this was two years ahead. So, great things can happen by giving people that context and safety.
Karen Mangia
You hit at another important leadership or entrepreneur principle: we all feel greater ownership of what we helped to create. And sometimes, the most challenging thing as a founder or leader is to let go of something you've created because the team highlights a better way. I'm guessing you spend some time coaching people on discerning when to be a leader who says, "I know the way we're going—this way," versus "Hmm, perhaps there's some merit to what you're saying, and I need to let go of the reins.” How do you coach people on striking that balance? Because we all hang onto things we created because we feel great about them and we see how much work we put into it. Sometimes we think we know, even if we don't. How do you coach people through that process of when to double down and say, “This is the way forward,” versus when to be open to completely changing direction?
Tissa Richards
The question of completely changing direction is an interesting one. When you think about the story I just told you, it wasn't even completely changing direction. That was to get us to the direction of the company. When I'm coaching people or talking to executive leadership teams or boards, there's the question: What's the macro strategy? That's one thing, the details of how to get there. If you're thinking of a group hike, at the end of the day, you want to get to the other trailhead. If the team says, "You know what, we might want to try going on this trail versus that trail, we might want to do X, or we might want to take a little detour to the scenic place, but that means we know we're going to have to hike extra fast to make up the lost time." It's the more micro level: How do we get to the end destination? So sometimes, it's about the journey rather than the destination. If you're also trying to control the journey, there's time to coach people and say, “Are you also controlling the journey because people need to be able to fill in their roadmap sometimes?"
But that's part of the role of a board. That’s part of the role of the ELT, where do we need to be and why—is it to hit revenue targets? Is it to hit customer deployments? But can we give people a lot of space to figure out if there might be a better way? There might be some features that would be great if we could add them in as long as it's within the envelope of our budget. But micromanagement? No one likes to be micromanaged. And we're adults. Let's not micromanage adults. And if you need to, did you choose the right team?
Karen Mangia
And speaking of boards, you coach people, help them get into first, second, and third board positions, prepare them for that journey, and support them. Many readers aspire to be on a board, yet it feels like a mysterious black box. How does one get on a board? What would people need to do to get ready? Please give us a little express coaching on becoming a board member.
Tissa Richards
It's incredible how many people have this goal and that it's almost secret. The first thing is: don't make this goal a secret. That is my first piece of advice. People need to know what you want to do so that they can help you.
It's the same thing, by the way—and it's not exactly your question—but if you want to get into the C-suite, if you want whatever your goal is, don't keep it to yourself because your network is your most valuable asset to you. If you have an aspiration, don't hide it. Tell people if you think you'd like to get on a board. I think it's also necessary to realize that the role of a board is to help set strategy and reduce risk, so consider how you can do that. However, a board versus an executive operating team is not operational. I love this saying of noses in, fingers out. You're not doing on a board; you are helping set strategy; you're assessing the team, but you're not operating. You're not rolling up their sleeves and doing. We want to translate, especially if you come from executive leadership where you're still active as an operator; we want to translate your accomplishments that are more on to the strategy.
It's even more important to be able to say: So what? How is that going to help a company set strategy or reduce risk? Get hyper-specific about yourself. Who do you support? Why does it matter? Be bold and specific. What kind of domains can you help? How does that help create value?
Even more specifically, leverage your LinkedIn. Put in your headline things like board and board advisor. Start advising companies; the more you do, the more people will see your value. As an aspiration, so many people will say I want to start on a public company. It is rare to get your first board to be a public company. So, look at startups; look at earlier-stage companies. Start there.
Think of your message. Be specific. I love this as a script: “Hey, you know I'm known for this. I'm looking to add a board to my portfolio. Who do you know that I can help?"
Not: “Who do you know that has a board seat right now?” Start having conversations with CEOs, with board members where you can let them pick your brain, give some advice. And the more you do that, the more people will realize you have a lot to offer.
Karen Mangia
You have to speak about yourself, not in terms of what you've done but what you can do strategically for the people that you're hoping to serve. Don't keep your aspirations a secret in any area of your life, whether that’s doing a triathlon, getting on a board position, accessing the C-suite, whatever that might be. I love your simple conversational framework for how to make that ask: start small, ask people whom you can help, be helpful, and it will spread out from there. There will be a preponderance of goodness.
Given your work with private equity firms and your fundraising experience, what advice would you offer to people trying to raise money right now because it is a challenging environment if you're looking for funding. Based on your wisdom and the private equity firms you spend time with, what advice would you give to every founder looking for funding?
Tissa Richard
I would raise money very differently now if I were doing it again. One of the things that a lot of founders and CEOs need to do is learn that they can also be in the driver's seat. You're so desperate for capital, a lot of time that you will take any behavior; you'll take any backpack; you'll take anything because money keeps you alive. What's interesting is—and this loops back to our discussion about values and non-negotiables—I tolerated a lot of behaviors and a lot of commentary that I wouldn't today, which may also be the result of age and wisdom. Many funds said they were early stage, pre-revenue, and then when I got there, they said we didn't have revenue. Is that not the definition of pre-revenue? Having that ability to close down a meeting quickly is important. If it isn't a match, great. Let's not waste anybody's time.
Also, asking questions. I frequently didn't ask any questions; I felt like I was being grilled. Take the time to ask questions. How do they do business? What are their values? What non-negotiables qualify them just as much as they're qualifying you? We're afraid to do that as founders because we're so desperate for capital, but we realize in desperation that not all dollars are created equal. You can find yourself in a position where you have the wrong investors that are a values mismatch with you, which can be far more dangerous than being undercapitalized.
If you are further down the road and they may invest, talk to their previous investments, talk to their last portfolio companies, talk to the ones that went wrong, the ones that failed. Find out what they're like. It's all kumbaya at the beginning. Find out what it's like when it's not kumbaya, because you will set the culture for your company and your teams. Find out what the culture will be like with the people who will be on your board and will be asking you tough questions. You need to ask them hard questions, too. This is not squishy. This is critical.
Karen Mangia
What you're willing to settle for is the difference between a scarcity mindset and an abundance mindset.
With all the work you've been doing, what do you want your legacy from the work you're doing now to be?
Tissa Richards
I want my legacy to be a group of very unshakable leaders who know what their own legacy is. So, helping people do that—knowing they're so what; knowing their values that have been unshakeable in the face of anything that happens to them, whether that’s personally, or with their teams and their companies. I think that comes from helping them figure out their value so they can stand up and say, “This is what I'm known for. This is why it matters. And this is how I lead my teams and my companies."
Karen Mangia
Well, thank you for that. Now, we'd like to switch to a little more fun section of the virtual water cooler interview because people say they miss this spontaneous experience of bumping into someone and having a casual conversation. So, imagine you and I are wearing cowboy boots and, you know, we roll into the break room together for a little casual conversation. I'm going to ask you five quick questions. You say the first thing that comes to mind. Are you ready?
Tissa Richards
Okay.
Karen Mangia
What time of day do you do your best creative work?
Tissa Richards
Either 2 PM or 8 PM.
Karen Mangia
Speaking of time, if you had an extra hour daily, you now have 25 hours instead of 24. How will you spend your additional hours?
Tissa Richards
Reading or walking my dog.
Karen Mangia
If you had to eat one meal every day for the rest of your life? What would it be?
Tissa Richards
Can I ask a clarifying question? Is this a calorie-free meal?
Karen Mangia
Oh, yes. This is not the time to pick the egg-white omelet with spinach.
Tissa Richards
Okay. It would be sourdough toast with hummus, melted cheese, and a nice tomato from my garden.
Karen Mangia
Oh, that sounds delicious and you're making me hungry. So, I'm going to need my extra hour to eat. Now, imagine the zombie apocalypse is coming. Who are the three people you want on your team?
Tissa Richards
I want somebody funny. Somebody handy who can make a shelter and knows how to start a fire. And I want somebody who can speak several languages.
Karen Mangia
That is a great skill mix, especially the multi-languages—very wise. And last, how can readers learn more about you and stay in touch with you and your new thought leadership?
Tissa Richards
Yeah, so my website is eponymous, so it's tissarichards.com. And there you can find my courses, my keynotes, and my corporate workshops. You should reach out there!
Karen Mangia
Thanks to founder, author, speaker, and coach Tissa Richards for sharing her insights on the Success from Anywhere blog. Because success is not a destination.
Success is not a location.
Success is available to anyone, anytime, anywhere.