777 Tissa Richards: No Permission Needed

Founders spend a lot of time pitching angel investors and VCs and as they judge your startup – its team, its market, its product, its traction – it’s also important for the entrepreneur to be assessing and qualifying the investor. Because like serial entrepreneur Tissa Richards shares today, not all money is created equal and sometimes it is better to walk away from a deal than to take the dough. The trick is knowing your value and your non-negotiables.

MELINDA

Hi, I’m Melinda Wittstock and welcome to Wings of Inspired Business, where we share the inspiring entrepreneurial journeys, epiphanies, and practical advice from successful female founders … so you have everything you need at your fingertips to build the business and life of your dreams. I’m a 5-time serial entrepreneur and founder CEO of Podopolo. So wherever you are listening to this, download Podopolo, discover great new podcasts, and join the Wings community there to take the conversation further with your questions, perspectives, experiences, and advice for other female founders at whatever stage of the journey you’re at! Because together we’re stronger, and we all soar higher when we fly together.

Today we meet an inspiring serial entrepreneur who has made it her mission to create a legion of leaders with an unshakable sense of self.

Tissa Richards is a repeat software founder who has raised millions of dollars for her companies, won awards for innovation and products, and holds multiple patents for complex cybersecurity software, and now sits at the intersection of entrepreneurship, fundraising and executive leadership. Tissa works closely with founders of hyperscale companies as well as Fortune 1000s to create strategies for fearless, authentic, and resilient success, develop high-performance cultures, and to diversify C-suites and corporate boardrooms.

Do you really know your own value? Do you have a quiet confidence about your ability, the ‘swagger’ of knowing whatever life and business throws at you, you’ll find a path to success? Do you know your boundaries and your non-negotiables?

All too often women entrepreneurs struggle to confidently articulate their accomplishments – or set clear non-negotiable boundaries around how they want to show up in business. If like many women you have that people pleasing perfectionist gene, listen on because it could be standing in the way of game-changing success.

Tissa Richards has learned from experience as a serial entrepreneur raising millions for her many startups why knowing your value – and developing presence, credibility, persuasiveness and what Tissa calls “swagger” is critical to your next leap as an entrepreneur.

The blueprint is in Tissa’s bestselling book “No Permission Needed” so make sure you get that, and today we dig deep into what can stand in the way of women founders, including why it’s vital to qualify your investors as much as they are qualifying you. Tissa creates strategies for fearless, authentic and resilient success, and who better to give you advice than someone who has truly been there and built that. We talk about fundraising, self-care, team building and much, much more.Let’s put on our wings with the inspiring Tissa Richards and be sure to download the podcast app Podopolo so we can keep the conversation going after the episode.

And we’re back with Tissa Richards, serial tech entrepreneur, trusted advisor to entrepreneurs and F1000 boards alike, and author of “No Permission Needed”.

Melinda Wittstock:

Tissa, welcome to Wings.

Tissa Richards:

Thanks, Melinda. It’s so great to be here.

Melinda Wittstock:

You have “been there, built that” many times. You’re a serial entrepreneur, so you know the ups and downs along this path of entrepreneurship. Looking back, when you connect the dots, what’s the biggest single lesson that you have learned that if you could tell your younger self and other women who are potentially able to build big nine-figure and even billion-dollar businesses, what would that be?

Tissa Richards:

Well, there’s two lessons. I think the first is to make sure that you know your values and your non-negotiables so that you choose people, and that’s both your investors and your team, that are really aligned with that, because if you don’t, I think you can find yourself in some tricky situations. And I think the second is that if you’re not thriving, your company is not thriving.

And it’s so easy to work ridiculously long hours, seven days a week, 14, 15 hours a day, and to do that for years and realize that you are completely burned out, your cup is empty, and you can’t give to a company and a team that way, but you think you have to, because the work is always there. But if you don’t take a little bit of time to recharge, you can’t actually build a company with a lot of value. I had to have friends step in and pull me away and take me away.

Melinda Wittstock:

An intervention.

Tissa Richards:

They did, actually. I’ve never thought of it that way, but it was an intervention. But when they did that, even if it was just for a day, I realized that I was just that little bit more recharged and I was able to give what I needed to. So you think that you can’t do it because the work is there, but the secret is, the work will be there the next day. You’ll just have more energy for it.

Melinda Wittstock:

Gosh, 100%. I’m going to start with that last point first about really prioritizing self-care. This is episode 777. And, Tissa, every female entrepreneur has had this issue with burnout, because I think we’re kind of naturally wired to be people pleasers. Women’s role in society for millennia has been like, “Let’s make sure that everybody is okay.” And so, we end up putting ourselves last, which is actually the worst thing that we could do for our businesses.

Tissa Richards:

Yeah. And I’m not even sure looking back if it was just me trying to please people or if it was just that sense of, “Oh my God, if I don’t have my foot to the pedal at 150% at all times, I will not succeed.”

Melinda Wittstock:

Right. Yeah.

Tissa Richards:

And it wasn’t until I realized how empty my cup was that I thought, “I can’t succeed regardless at this pace.” And I don’t even think the word self-care were really in the nomenclature when I was running my start-ups, but knowing that, you just can’t… When you are burned out, that’s it. You’re burned out. And I think, finally, it’s in the dialogue. It’s commonplace to say, “You have to prevent burnout. You have to be able to have the energy to be creative and to think and to give to the company.” And so, it’s okay to say, “I’m going to turn off my laptop and I’m actually going to take a weekend.” You may not have the budget to go somewhere because chances are you are-

Melinda Wittstock:

Yeah, all your money is in your start-up.

Tissa Richards:

Your money is there.

Melinda Wittstock:

Yeah.

Tissa Richards:

At any time, you can just turn it off and do nothing and go for a walk with your dog, but I didn’t even do that, and that’s really dangerous. Truly, if you’re not thriving, no one around you is thriving and your company is not thriving. And if your investors aren’t seeing that, for example, they’re not the right investors, or if you’re not able to negotiate a salary for yourself, even if it’s a small one, that’s going to take a toll on you. So those are things that I think we need to start really advocating for founders.

Melinda Wittstock:

And that gets back into that non-negotiable, and I know so many female founders who are like, “Okay, I’m just not going to pay myself.” And so, finally, you get the money and you’ve set the expectation and the bar of what you’re going to be paid or whatever. You’ve trained your investors that you’re okay with that and such. And, I mean, that’s one of the reasons with this one, even though we didn’t have the cash to pay me my value in building this. I have accrued compensation. At least it’s in the books. Whether I take it or not or when’s the right time to take it, that’s a whole other question, but at least it’s in there.

Tissa Richards:

I’m so glad, right? And I can’t tell you how many times I hear founders now say to me, “Well, my investors have told me,” or “I feel like it’s okay. I have equity.” Well, the vast majority of companies fail, I can’t tell you how much equity I have given people as a form of currency, and usually it turns out to be worth nothing. You can’t buy groceries with equity. You can’t pay your mortgage with equity or your rent with equity. You need some form of liquidity for yourself as well.

And there’s another thing too on the flip side of that, which is to make sure that you’re also properly advocating for yourself, just even in your term sheets. I had a founder come to me and say, “Hey, my investors are going to do invest in…” I think it was the third or fourth round, and they want to have a term in there where if there’s any future cap table disputes, I’ve got to settle that dispute out of my own equity pool.

Melinda Wittstock:

Oh, gosh. What?

Tissa Richards:

Yeah. And she said, “It doesn’t feel right, but they said if I don’t sign it, then they’re not going to invest.” And I said, “Well, if it doesn’t feel right, we need to talk about that,” because if they’ve done three or four previous rounds of due diligence, there shouldn’t be any question about the cap table, and it’s that ability to feel confident enough to say, “This doesn’t feel right. It doesn’t feel just.” So not only does it not feel right, but it is not right, and feeling confident enough to say, “Money is not everything here, but the right thing is also important.”

Melinda Wittstock:

It takes a lot of the female version of cojones to turn down money because it’s so hard to come by. We still have this stat that only 2% of female founders that are qualified for venture capital money actually get it, a number that hasn’t really moved in many decades. It looks like it’s sort of beginning to change a bit. So if you’re in that scarcity mindset, which there’s a lot of evidence that would force you into that mindset, it’s really easy to panic and take money. But the wrong investor? Oh my gosh, what a disaster.

And so, I know, Tissa, that you’ve had experience with that. For anyone listening to this podcast that’s out raising money or has raised money or whatever, talk to me and everybody about how to know that you have the right investor and how to make sure there’s alignment there and the downsides of not doing that.

Tissa Richards:

Yeah. This is a really interesting topic, Melinda, because I think you’re right. By nature of the game, you almost have to come from a scarcity mindset because you need money to spend money. You need money to make a company grow and to pay bills. But there are times where I will say to a founder, “First of all, all money is not created equal.” So a million dollars from one investor is not the equivalent of a million dollars from another, and not just from a term sheet perspective. Terms are important, but the person or the people that you’re taking that money from are also as important.

And I think there are times where… And this is a hard truth, but if that person, if it doesn’t feel right, if those people don’t feel right, if you don’t get a good feeling, or if you just feel like you’re really misaligned, it may be the best thing to shut that company down. And that’s such a hard thing because you’ve put so much blood, sweat, and tears. You’ve probably put most of your own savings, and you feel like the opportunity cost is so big that you should just take the money.

But how do you know that those are the right investors? I can tell you, most founders don’t go and talk to other founders that those investors have invested in. There’s such an imbalance of power there. But why don’t we check references? It’s a strange thing, but why don’t we do that? What is this person like to have on your board? What are they like to have on your cap table? What are they like when things go bad? And we, as founders, tend to be asked all the questions and not feel empowered to ask questions ourselves, I think, because we’re so grateful to get a check, but those are really important things to do.

Melinda Wittstock:

Oh my goodness, that’s such good advice. One of the things that I’ve really started to do in the context of Podopolo is really look at, “Okay. So who are their portfolio companies? Do any of those portfolio companies at all have a female founder or a female CEO?” And then, okay, I really want to talk to that person and get advice. What are they like? Whatever. And worst-case scenario, you find out that, “Oh, God. Yeah, I would dodge a bullet if I didn’t take investment from them,” or “Yeah, they’re great,” and you develop a relationship. Maybe you get a warm introduction to that investor from a founder, which is arguably more valuable. So much of this comes down to relationship.

Tissa Richards:

Yeah. And somebody suggested this to me, which I thought was really interesting, especially considering some of my background, and the advice came too late, but that’s okay. But also talk to failed investments, because think about a relationship, a marriage, or… When things are good, things are good. When things are bad, that’s when you really find out what people are like.

And so, a failed investment can really reveal to you what things are like and what people will be like to work with when things are hard, and I think that’s when you also get a sense of someone’s values or that what it will be like to be in a board meeting with them or on a call with them when all hell is breaking loose, and that’s because, hey, if everything is going well and your valuation is going up and you’re hitting your revenue targets, it’s kind of kumbaya. But when it’s not, that’s when you want to know what is that team going to be like, what is that dynamic going to be like.

And you could ask a prospective investor, but they’re not going to tell you, “Here’s what I’m like when my claws are out.” But you want to know, because some people are very collaborative. They’re very helpful. They acknowledge that things are out of your control. And I think understanding what it’s going to be like through the good and the bad is really helpful because it’s stressful enough even when things are going well.

Melinda Wittstock:

Right. So I know you’ve had experiences at both sides of that equation, right? Because people are pretty attached to their money, and a lot of VCs have this model that only one in 10 has to work. So the minute it’s maybe not working, you’re not suddenly getting the support you need from them because they’re putting all their eggs into that one that’s going to get them the return, and the rest of the other nine, oh well. There’s that.

Is there any specific experience that you’ve had that really taught you this? Because I think we all learn from when things go wrong as entrepreneurs, more so than when they go right, because when they go right, it’s kind of like, “Oh, well, that was easy,” and everything’s great, right? But those tough times, and there are many, truthfully, if you’re setting out to build something that’s really innovative or is changing behavior or is a major swing for the fences, like you’re going for the unicorn status or whatever, you’re aiming big, there are certainly going to be lots of challenges along the way that you don’t even anticipate. So what are some of your specific experiences that you went through, and what did you learn from them?

Tissa Richards:

I think sometimes you obviously want to take advice from your team, that includes your investors, but also follow your gut. I mean, we had, as an example, in raising a subsequent round, the advice to put our valuation at a certain number, and it seemed really high, but that was what we were hearing from a number of people, and my gut just told me that it didn’t seem reasonable. But at a certain point, when enough people tell you that, you think, “Okay. I guess we should do that.” And even as a young founder, I think listening to your gut is important. You want to take as much input as you can, but don’t not listen to your gut. It’s there for a reason. That inside voice is an accrual of a lot of your experiences.

And that can be a scary thing because you think, “Well, why do I have all these advisors? Why do I have all these people around me?” And I think, in hindsight, I probably should have listened to my gut and not the voice of a lot of external people. So I think, listen to your gut. Don’t take money out of what we talked about, which is that scarcity, but sometimes you do have to, because otherwise you will have to shut down. Yes.

I also think another thing is, spend money on lawyers earlier. A lot of start-ups leave it too late. They’re expensive, but it’s very important because you kind of cover your bases and, in the end, you save more by getting proper advice as opposed to trying to wing it. And I think another thing that I probably waited too long was, offload the things that you don’t like to do. For example, I should have brought in a controller and a CFO earlier. I didn’t like it. It wasn’t my strong suit, but it seemed like an expensive expense. When I did it, I thought, “Oh my God, why didn’t I do this earlier?” It helped with fundraising. It just helped with clearing out headspace. So really think about not just is it strategic to do, but will this free me up to do other things? Those are just some of the thoughts.

Melinda Wittstock:

Well, that’s exactly where I am right now in the context of a Chief of Staff position for Podopolo. Jeff Bezos had this at Amazon right from the beginning, that he called this person his ‘shadow’, which is kind of a weird word. But the operational integrator, taking a vision and operationalizing the values, getting all those systems in place, the person who can be you as a visionary founder in the day-to-day minutiae.

Now, in my previous start-ups, if I’d had that person much, much earlier, what a difference that would’ve made. So at this stage of Podopolo, that’s a critical, critical hire.

But do enough founders really understand what their unique zone of genius is, double down on that, and hire the rest early enough? I think that’s a real issue for women because I think we get afraid of adding too much expense too early, rather than seeing it as an investment. In your start-ups, Tissa, what was your experience with that in terms of when to hire for these different positions relative to your own strengths or weaknesses?

Tissa Richards:

Yeah. And this is so hard, Melinda, because your cash is so, so scarce. And so, you really think, “Well, I can’t bring these people in.” It’s that trade-off between who are you going to bring in that’s going to start to generate, let’s say, revenue or growth versus can I also bring someone in too? I love what you’re saying, like the shadow. I like to think of a Chief of Staff almost as your proxy. Somebody who can at least maybe help as a CEO or founder offload some of your brain space or your overhead, mentally, physically, whatever it is, so you have more space to scale.

And that’s a hard trade-off, because you know there’s pressure from your investors. Get to revenue, get to growth, get to proof points. But you can’t do that because you can’t be in six places at once. So it’s a really hard decision. Where do you deploy your capital early on so that it grows the fastest? Sometimes, there may not be a direct, linear relationship between where you’re spending that money and seeing a return on it in a very clear way, if that makes sense.

But if what you’re getting is you’re not burning out, you are quickly offloading some of your stuff so that you can be out in the field with customers, with prospects, with investors, that’s a good ROI too. It just doesn’t have as linear of a relationship in your projections as an example. I wish more investors would understand that, I think. It just doesn’t have an Excel formula or an equation.

Melinda Wittstock:

Well, exactly, because you’re basically hiring a Swiss Army knife that is really going to advance all of those things, so I think of the Chief of Staff position. So interesting, because it can really make the recruiting and the onboarding process much better. It can align information flows so decision-making is better and made with full knowledge that everyone on the team is communicating properly, especially if you have a very cross-disciplinary team, that everybody’s aligned.

And then that’s a huge value to get that right because it makes everybody else much more effective and, frankly, speedier and better at what they’re doing. And again, this is the reason why start-ups like this need funding because you’ve got to spend to be able to maximize. I’m curious what you think about this. I think a lot of us think, “Oh my goodness, the investors that are sitting in judgment of us are brainiacs. They’re really smart, they know everything, and I’ve got to justify myself to them.” And then you come to realize that actually, no, that’s really not necessarily true at all. And in fact, a lot of them have no operational experience whatsoever, so they have no idea whatsoever about-

Tissa Richards:

You’re inside my brain. That’s what I think. Yes.

Melinda Wittstock:

… how to build a business. Right?

Tissa Richards:

I think, yes, many of them are business school graduates. They’re very on the theoretical side. You’re right, but they’ve never been an operator. So they’re asking you or they’re sort of suggesting operational expectations or things that aren’t really executable in the real world. Yes, this is an eternal struggle between a true operator and a theoretical investor.

Melinda Wittstock:

So there was a certain point, Tissa, where… Maybe you decided, okay, after launching all these different start-ups, some of them that really did well, got to exit, other ones that did not, there’s a certain point where you’re looking at yourself thinking, “Am I going to do this again?” What is your thesis about that? Is it once an entrepreneur, always an entrepreneur? Can you not help yourself in a way, or is there a certain point where you say, “Okay, enough”? And what’s that line been for you?

Tissa Richards:

Melinda, I call myself a recovering founder and CEO, and I don’t want to make light of addiction, but I say it because I worry I’m going to wake up one morning and go, “Oh God, I started at a software company and I miss touching technology and I miss touching innovation.” But I think at that point, and let’s be really, really real for a minute, I think very few people have truly lucrative exits that create generational wealth. And so, you reach a point where you really have to ask yourself, is this something that you can continue doing over and over?

And it takes a toll on your physical health and your relationships and your mental health, and I think I just thought, “My cup is so empty. I’m so tired.” It had impacted my health, and I thought, “I just want to take a little break.” And I truly thought I would go back and do it again. But in the interim, I started to do what I do now and realized it was so fulfilling on every level. And who knows? You can never say never. I still know what my next two technology platforms would be if I ever was crazy enough to want to raise money again, but I think I can…

I have a platform now, I think, to also help and guide founders, but to do it at a little bit more of an arm’s-length distance. So it’s really fun, and I love every day of what I do now and don’t have to be in the firing squad line, if that makes sense.

Melinda Wittstock:

All the lived experience that you’ve had, Tissa, is so valuable in advancing others and particularly women. There’s no need to reinvent the wheel. We do have, if all of us get together, an extraordinary hive mind for avoiding. Why should any women fall into this trap ever again if we all got together and shared this knowledge? So it’s amazing what you’re doing, working with Fortune 1000 on hyperscale companies, really giving them these blueprints, whether it’s culture or diversification and such.

Tell me more about the work you’re doing and actually what you’ve learned along the way, not only in terms of what people need most from you, where the biggest issues are, and how it’s going for you. What are you getting from it?. And also, what you’re getting from it in terms of the vocational satisfaction of that.

Tissa Richards:

I think what I really focus on now is helping individuals, teams, and organizations just create this unshakable sense of self, and that really enables them to, I think, create a lot of value, a lot of focus and mission. And it is really fulfilling, and I think it really dovetails well with… I’ve been described as super pragmatic and efficient and practical, and I love when people can be inspirational and things like that, but a lot of times, I think if you just meet somebody or hear something that’s inspirational, you’re left hungry and you think, “Well, what am I supposed to do with that?”

So one of the things I really love to do is, how do we move the needle in just a very practical and pragmatic way? So whether it’s the book or the keynotes or the workshops that I do with companies, I really like to get to, how do we make organizations and teams really, really efficient, work really well together? And I think a lot of that comes down to, who are the people? How are they working together? How are they communicating? What’s the purpose of that group or that company?

And I think, having raised money, having built these really high-functioning teams or high-performing teams, I’m really good at coming in and sort of saying, “All right. What are we trying to do? What’s not working? How do we turn this ship and get everybody paddling in the same direction?” So it’s just really… It’s fun. It’s very high-energy work, and it’s very impactful. And like you said, a lot of it is also about taking people who maybe weren’t in those positions before or diversifying those teams and just seeing people really, really thrive, and I pinch myself a lot because every day is different and really enjoyable.

Melinda Wittstock:

What are you seeing from women and the difference between women and the way they tend to build teams or lead teams as opposed to men?

We’ve had a lot of guests on this podcast recently who really have highlighted the fact that women’s natural empathy or the archetypal feminine qualities of that kind of intuition, we were talking earlier about trusting your gut and such and being more relationship-oriented, are really creating different ways of building and motivating teams. How do you see that playing out?

Tissa Richards:

It’s interesting because a lot of the work I do is with women, not exclusively at all, but I’ve always really focused on not actually focusing on gender, if that makes sense. So it’s almost like the work that I do to diversify the C-suite and the boardroom is actually almost an unintentional byproduct of helping people just show up, get the work done, learn how to talk about why the work they do matters, how they lead, but not focus exclusively on how they’re different. Does that make sense?

Melinda Wittstock:

Right. Oh, it does. I mean, it’s a wonderful place to be at, where we don’t have to think about it in those terms anymore.

Tissa Richards:

Yeah. Yeah.

Melinda Wittstock:

And there is a lot of comparisonitis in that sense. Do men do militaristic, command-control kind of operations and women do more relational ones? Well, no. I mean, a lot of men are really becoming a lot more focused on the EQ part of this, the relationship, the servant leadership, or whatever kind of language we want to put around that.

Tissa Richards:

Yeah. I was introduced to a really interesting concept called the decency quotient, and it’s this idea of EQ, IQ, and what they call DQ, which is so fascinating. And it’s this idea that I think everyone can benefit from learning how to be a better human, a better leader, and really focusing on essentially how to lead people better, communicate better, listen better, and I think that’s a lot of the work that I do, and that, I think, just makes for better teams, better cultures, better outcomes.

Are women maybe naturally better at some things than men or vice versa? Possibly. I could tell you I’ve seen really, really lousy female leaders and really lousy male leaders. I think you can over-index on the gender piece. I think there’s certainly some data, like you talked about, who gets funded and things like that. But I really like to just help people learn how to show up, be prepared, be an amazing communicator, and I think that’s how you really get ahead.

Melinda Wittstock:

What are some of the biggest mistakes that you see leaders, CEOs, at any stage of growth-making, be they men or women, where you really help change the game for them?

Tissa Richards:

This is so interesting, Melinda, because this just happened yesterday. Of course, January is a time of performance reviews and feedback and things, and somebody told me that they were criticized for saying the words, “I don’t know.” And I actually think that that’s one of the most powerful things you can say. When I was raising money, I would never say some… I would never pretend to know something I didn’t, and that’s really why I would bring a lot of people from my team with me if we were meeting partners or customers or investors.

And I think that a big mistake is to actually pretend to know something you don’t. Show up as prepared as you can, but isn’t there more power in saying, “You know what? I don’t know the answer to that. Let us get back to you. Let me get back to you. Let me go find someone on my team who’s an expert on that”? And I think an extension or adjacent to that is, the person in the room who talks the most is usually not the most influential or powerful.

So helping people let go of the need to be seen as the sole expert, but also the person who’s commanding the room. You can be very commanding and have a big presence, but not be the most dominating. So it’s kind of learning about influence and communication and presence without being overbearing. Does that make sense?

Melinda Wittstock:

It does. You observe how really successful people walk. They never look like they’re in a rush. They’re going at their own pace. There’s sort of a quiet confidence about it, as opposed to someone striving to be taken seriously or to get to that next point or being in that grind. There’s something about how we see our own value subconsciously or just consciously, even consciously within ourselves and how it expresses and how it then transmits to others. And not only knowing your value, but actually embodying it in the way you lead.

Tissa Richards:

Absolutely, and it’s been so interesting to watch how that manifests. I did lots of body language and where do you sit and how do you sit at a table and things like that, but then we shift to the pandemic, and how do you embody presence and confidence over Zoom or not be spoken over, for example, over Zoom? And so, that’s a whole different set of skills to learn, but there are ways to have that quiet presence or loud presence of some people.

But there are ways to really build up a lot of credibility, a lot of presence, and authority even, without being loud, and I think that’s something I see a lot of maybe CEOs or super senior people need to learn, and just listening. And I think very loud people or people that really want to lord over their authority and position, they can actually make a lot of progress by learning how to tone it down a little bit, but still be authentic. I mean, authenticity is also really important, not putting on someone else’s persona, because that’s exhausting.

Melinda Wittstock:

Oh. Oh gosh, for sure. And so, I think a lot of people, a lot of founders, because, by definition, you haven’t done it before. In fact, no one’s done it before in really disruptive companies. And so, there’s bound to be some self-doubt. So what are some of the traps there or impostor syndrome or whatever, where maybe there’s a tendency to overcompensate and look stronger than you actually are, or the whole fake-till-you-make-it phenomenon and all that kind of stuff? Is that just all masking for self-doubt?

Tissa Richards:

So I think this is really interesting, because at the same time, one of the things I work on the most with my book is actually how to overcome self-doubt. But in the start-up world, I had a great mentor who said, “As a company, act like a big company. Cast a big shadow.” I mean, literally, do the things as a company. Get a board very early on. Put great governance and processes in place. So be like a big company, but don’t be brash and arrogant. So strike that balance.

But when it comes to self-doubt, I think it’s really interesting, because I always say, especially with women, “Your value is a fact.” So a lot of people will say, “It feels arrogant to get in touch with how to get rid of that.” But I like to think of it as three Is, right? Identify what you bring to the table, why it matters, how it creates value, and then internalize that, and that’s really where you can kind of close that vacuum.

And how do you internalize it? Well, number one, you realize it’s a fact. I love to… It’s almost like me… What are those things that people do? Affirmations, but in a very specific way. Say it out loud. Pretend you’re on a podcast. Pretend you’re giving a keynote. My poor dog is so sick of hearing me talk about my keynotes and workshops out loud, but the more you say it out loud, the more real it becomes. And then the third I is really-

Melinda Wittstock:

So you’re making me laugh so hard because I was doing affirmations to poor Auggie, my golden retriever, because he looks at me in the eye and I do my affirmations for him. He’s on board with it. He’s good.

Tissa Richards:

Oh, so you know, but I had a woman say to me after a keynote, “Well, I do affirmations. I say I’m smart, I’m whatever.” But I think, “Let’s be specific. Don’t just walk around saying, ‘I’m smart, I’m great.’ Literally walk around your house and say, ‘My work matters because, I move the needle because, these are my non-negotiables because.'” I think specificity is the soul of the story in that sense so that you’re actually practicing saying out loud why what you do matters, why you matter, and that’s that sort of internalization and that leads right into that third I, which is informing or communicating.

And that’s going to get you to really practice, whether it’s to interview, how to raise money, how to be in a networking situation, so that you’ve said it out loud so many times and it just rolls off your tongue in a really concise and compelling way. And I guarantee you, there’s quantitative and qualitative benefits to being comfortable with who you are and why who you are matters. I see it all the time with the companies and the leaders that I work with.

Melinda Wittstock:

Yeah. So, I mean, if you can say it to your dog very confidently, you can say it to anybody, but I love the specificity around it. It’s not just like, “I attract abundance into my life.” Yeah. Okay. Abundance of what?

Tissa Richards:

Right. That’s right. Yes.

Melinda Wittstock:

I mean, it could be not necessarily positive abundance.

Tissa Richards:

Yes. Yes. Specificity is really important in all areas too.

Melinda Wittstock:

Oh gosh, 100%. So in your book, you talk about swagger, and I think we’ve sort of started to touch on this idea of quiet confidence, but I love the word swagger, especially in the context of women. So talk to me about swagger.

Tissa Richards:

I’m going to give you an example. I had a client who got to the final rounds, two candidates for a CEO role, and she didn’t get it, and the recruiter told her, “You…” The feedback we got was in the final interviews with both the management team and the board. “You kept talking about we. We did this, we did this, we did this. And we’re not hiring we. We’re hiring you.” And she said, “I guess I’m still really uncomfortable talking about me and I.”

And, I mean, I speak to tens of thousands of women a year, and that is a universal problem, is they will say to me, “Well, I am not the only person that did this.” Of course, we know that. You’re not adding a modifier to say, “I am solely responsible for X accomplishment.” But it’s really important from a cognitive load perspective for people and just to make it simple to walk up and own your accomplishments, walk up and own why we should care, and that involves saying the words, “I, I’m known for this. I do this. I am perfect for this role because,” and that takes a bit of swagger.

And there’s a difference between swagger and confidence and arrogance, but arrogance is when you’re sort of saying that you can do something and it’s not based in reality or fact. Swagger and confidence are based in fact, they’re short and to the point, they’re in context, and you are bringing them out at the right time, in the right situation, and then you’re stopping to also listen and include other people. And I think, I know for a fact that when I coach women and we add a little bit of swagger to their delivery, to their communication, we get a lot of stuff done. We increase compensation. We land major sales deals. We raise more money, because people think, “Huh, she can do this. I believe in her. I have confidence because she has confidence.” It’s very powerful.

Melinda Wittstock:

I love what you said there, Tissa, because I’ve seen so many women, and I know I’ve fallen into this trap myself, of just sort of minimizing accomplishments. I remember in a female founder accelerator I was part of, Springboard, and they made us do, in this boot camp, a two-minute pitch about our company that we’d have to practice and nail that, and also a two-minute elevator pitch about yourself.

And there was literally a woman who’d had a $500 million exit who forgot to mention that in her two-minute pitch. There was another woman who was an astronaut, and she was doing this whole start-up related to that and didn’t mention that she was one of the first women in space. And so, it’s interesting to me. I’m looking at it right now from a slightly different perspective too as Podopolo is recruiting people, and I’m finding that the research is right that men will apply even if they profoundly don’t qualify. They maybe have one or two of the things. You say, “We need eight years’ minimum experience for a lead back-end engineer.” Right? And someone applies, they’re just out of college.

But I think women cancel themselves out of a lot of opportunities because they look at that list, and so, “I haven’t done all of them,” or “I personally didn’t do all of this. I did it as part of a team,” or whatever, right? So there’s a lot of canceling out too early in the game. What do you think though about women who are afraid to shout out their accomplishments because they’re literally afraid of judgment from others, and in often cases, specifically, sometimes other women? Like, “Oh, yes, you…”

Tissa Richards:

Yeah. I actually think women can be each other’s worst enemies, but I love to imagine how one of your wingwomen or your friends would introduce you. How do you introduce yourself? It’s probably very humble and maybe even boring, but I mean, how would I introduce you? I’d probably say you’re this kick-ass founder and entrepreneur that’s revolutionizing the podcast industry and you’re raising money and you’ve done all these amazing things, and it’s probably a lot more dynamic, a lot more memorable. And so, I always think, imagine that you have your cheerleader right there introducing yourself. Why don’t we cheerlead for ourselves in the same way?

Melinda Wittstock:

Oh gosh, I love that.

Tissa Richards:

But I think a lot of it is also in the delivery. So there’s a way to do it in a way that seems arrogant. There’s a way to do it in a way that seems very factual. And if it’s short and sweet and in context, then I think it won’t come across in an abrasive way. And this comes back to those three Is, right? Practice it. Practice, “I love this. I’m known for. I’m known for X. I’m looking to do this. What are you doing and how can I help you?” It’s so nonthreatening. It’s three sentences. It’s less than 30 seconds. And I think if we can sort of get used to that, we can really help each other, help ourselves, and not feel like we’re diminishing our responsibilities. It’s a very powerful thing, but I think it takes practice.

Melinda Wittstock:

It does, but what amazing advice. I know how I introduce you to all my team members, and you’re joining our board as our independent director, Tissa, which I’m so excited about. I feel so blessed to work with you, and I know how I introduce you

But I so appreciate you taking the time to come on the podcast. I feel like we scratched the surface, so at some point, you’re going to have to come back. In the meantime though, I really want to make sure that people know how to find your amazing book, No Permission Needed. It’s a number one release on Amazon, and it’s a must-read, frankly. What’s the best way?

Tissa Richards:

Thank you. Yes, it’s on Amazon and Audible, Barnes & Noble. You just need to google it, and you can also find more at tissarichards.com.

Melinda Wittstock:

Fantastic. And for people who want to work with you, that’s the best way too? Just check out your website, tissarichards.com?

Tissa Richards:

Yes, absolutely.

Melinda Wittstock:

Wonderful. Well, Tissa, thank you so much for putting on your wings and flying with us today.

Tissa Richards:

Thanks, Melinda. So great to talk to you.