Transcript

Think like an outsider, w/Shellye Archambeau, Ellevest’s Sallie Krawcheck, and Calendly’s Tope Awotona

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If I wanted to become senior. In the industry. The odds were stacked against me if no other woman had made it to the top. I've been an outsider my

entire life. I was not only the only black girl in my class, but I grew up being, frankly, bullied. Verbal abuse, physical abuse, gut. Pushed down, knocked down, beat up. I mean it was not good. So it was very clear to me. That the odds were in my favor.

I grew up in Nigeria and I just knew the traditional Growth playbooks wouldn't work for me. disadvantages can actually be advantages that I just had to do something different. That's Tope Awatona, founder of Calendly, and before that Shelly Rshambo, former CEO of MetricStream, and Sally Krachek, founder of Elevest. Speaking live at the Masters of Scale summit in a session called

Think like an outsider. I'm Bob Safian. Former editor of Fast Company, founder of the Flux Group, and host of Masters of Scale Rapid Response. I wanted to share my discussion with Sally, Shelley, and Tope. Because succeeding in today's chaotic economy requires doing things differently.

These three leaders learned that the hard way. By overcoming obstacles that might have derailed others. Sally was a pioneer on Wall Street, breaking the glass ceiling at institutions like Citigroup and Merrill Lynch. Shelley fought her way into the CEO's seat in the tech world, a rare black woman at the helm. Tope, who developed his entrepreneurial spirit in Nigeria, chose to build scheduling app Cowley in Atlanta rather than defaulting to Silicon Valley.

They were each outsiders and they continue to think like outsiders. Their stories aren't just inspirational. They're packed with lessons about how each organization and each of us personally can benefit from an outsider mindset. Let's get to it. Sally Krawak, geared directly next to me, founder and CEO of Elvest, tagline a financial company.

For women by women. Also former CEO of Sam for Bernstein, Smith Barney. insider enclaves. Toba Watana is the founder and C of Calendly.

Grew up in Nigeria. Now on Forbes Billionaire list, not via Silicon Valley. And then Shelley Arshambo, who grew up wanting to be a CEO and then grinding her way up the ladder at IBM, realized this is not gonna happen here if I do this this way. And she took a different tack to break into the corner office, which she did at MetricStream. She's now on the board at Verizon and Nordstrom and elsewhere. You're all terrifically successful. And also decidedly not traditional, and I think those two things are related to each other. Sally, you you have a a story you want to start us off with? Май сторі старцуа за твої секс є роль йог момен.

In investment banking at Solomon Brothers, so on Wall Street. And one day I looked up from the spread sheet I was working on. And realized I was the senior woman in my department. At the age of twenty six. And had a further realization at the time.

That if I wanted to become senior. In the industry. The odds were stacked against me if I did it the way everyone else had done it. No other woman had made it to the top. I was fortunate that my next job was as a research аналіст.

Because I also came to the conclusion as a research analyst that in order to be successful there. I had to really have something to add. My first research report. was on a life insurance company. Which was

growing in lending business. And all the analysts saw there's growth there. I said let me Dig deeper. And what I saw was a picture of deteriorating.

Credit quality. So I wrote my first research report. Called Wonelli. American general. And

I was right. We today call these loans subprime loans. And so I've approached every job I've had. With is there a different story and

Most recently in founding Elvest. I started to Really think through the problem. That women have thirty cents of wealth to every dollar a white man has. Black women have a penny. When you look at the drivers of this.

It's the gender pay gap for sure. But there's also a gender investing gap. My industry knows this. Then and their financial advisors. There's perfect product market fit between a middle aged white guy and his financial advisor. I love men. I've been married to a couple of them. There's nothing against

White men trust their financial advisor more than their doctor. The narrative is Women are risk averse. The narrative is women aren't as good at math or don't like math. The narrative is women need more financial education. Maybe.

What the industry is putting out is is perfect. And women are the problem, or maybe In an industry where ninety nine percent of mutual fund dollars are managed by men mostly white. Ninety eight percent of investment dollars are managed at companies run by men. Eighty six percent of financial advisors

Are men average age low sixties? Maybe they built the business for themselves. Maybe women Maybe women aren't just aren't buying what they're selling and what if we build the first wealth tech company Центр он.

There's still Much to be discovered if you step away from the conventional thinking. Shelley, you look like you have a question for Sally. Sally typically when you start something new and you're the first one to do it, which you did, obviously with Elvis. There's

Some unexpected. Things that happen. In that process. So what was most unexpected when you actually started this new model of trying to actually cater to the women who didn't have a model for financial advisors. Everything about a startup is hard. There's nothing that isn't difficult and you're always a step away from For those first. Months or years fr from failure.

I'd say one of the Biggest surprise is interestingly is when we launched and put out those first ads. That we're unapologetically for women. By women. There was a good double digit percent of women who said How dare you. We don't need something for women.

We don't need your dumbed down version. We don't need your Have a Chardonnay and let's talk about stocks together. Approach. Eventually they would go into the product and look at and come out and say, actually these are highly

personalized portfolios actually they take into account that women live longer earn less Salaries peak sooner, take more career breaks. So hey, this is more sophisticated. But what was really interesting is the messages we get from the patriarchy as women. That not one

Single Solitary woman. Said it's for women, it must be better. Not one. Енсо, де сопрацьовані о.

Gotta. Have a product that works and we gotta have a team that's great. That we actually are part of a cultural conversation. In which we're trying to reverse the point of view of Oh.

I'm risk averse. You know, when these things really aren't true. Mm-hmm. Yeah. So Tope, do you have a an outsider story for us? Oh man, do I.

I think all my life I've sort of been I know the odd man out from No, I grew up in Nigeria and I was you know. I love you guys too. Yeah, I grew up in Nigeria and I middle school I ended up giving a few grades. So which meant that in high school I was two years younger than my classmates, which is at that age. That's a big uh age difference. So just always sort of stood out in one way or the other.

But when I started Cowley In Atlanta in twenty thirteen, nine years ago. I was an outsider. Right, for many many different reasons. One, I didn't have a successful track record as an entrepreneur. As a matter of fact, I started and shut down four different businesses.

In addition to that, I was based in Atlanta, not in the traditional tech hubs of San Francisco, Seattle, Boston, et cetera. And Well, my background before that, I was in enterprise software sales, which is not really the background most people think of when you think of Tech uh CEOs and tech founders. So for all these different reasons, I was an outsider. And so recognizing that I was an outsider, I just knew the traditional Growth uh playbooks wouldn't work for me.

I could probably not count on raising large amounts of institutional capital. That's probably not gonna be a valuable Option for me. And so I knew that I just had to do something different. One, I knew that I had to be the first check in. There's no rich grandparent or gr uh rich parent that was gonna

Fund this business. And so I rated my four one K, empty it, even took out some loans. To start the business. In addition to that, I knew that I Needed a business model and a growth strategy. That wouldn't be incredibly capital intensive. And so

I ended up doing things like built a freemium business model so allowed a lot of people to use the product for free. That ended up uh driving virality and word of mouth and Till today still the biggest uh growth engine for the business, but at a very, very low cost. Because I wasn't spending a lot of time raising money, it also meant that I had more time to spend with customers and I knew their problems better than

Anybody else uh did switch allowed us to build a great product? And also when you don't have all the capital forces you to maniacally prioritize. So through a combination of All those different things. And I didn't uh raise a small seed to uh around in the early days of the business. We were able to grow the business to almost uh Hundred million dollars in revenue without any outside capital. Thank you.

Until today the company continues to be profitable. Which is a rarity for companies of our size and scale in our growth rate. And so The moral of the story is There are many, many different ways to sort of approach being an outsider. You can assess all your vantages and all your

Disadvantages and you can get hung up on all those disadvantages. But I actually think if you look very closely, those disadvantages can actually be advantages. as happened in the case of Cowley. So I think that's the uh the thing I would encourage people to think about. Turn those limitations into into opportunities when you can. Do either of you have a a question or a reaction to Top? Top. When you were building and scaling.

And you actually didn't have the dollars. Yeah. Right. Now as you're getting bigger, everybody wants to put money in. Right. So how what did you use as your framework? A lot of people here over time will raise money and all money is not the same. Sure. Any perspectives you might share about that part of it? We have Very, very ambitious.

Goals. It turns out that even in spite of the growth that we had and success that we had. There's still this validation. That sort of comes with institutional capital. There's still a lot of very smart people which the primary way in which they judge the quality of the business or the prospects of the business is whether it's been validated by an institution or capital. And oh, by the way, your customers too.

Especially for us we were looking to move up market and acquire more enterprise customers. There's a this validation that comes with institutional capital. So I think that what guided us in picking investors we wanted to partner with is do they have a track record of taking or working with businesses like ours to Celery their growth and I cheve better outcomes. Do they have a network? If you want to build a great business, it takes a village. Like you need all the ILAs you can in this a very tough journey.

Mm. I I love that. So uh even as an outsider, sometimes you have to be looking for things that can be your conduits to that insider community when you need it. Yes. What Sally Tope and Shelley are discussing here is how taking an unexpected approach can unlock opportunity. The status quo is always difficult to break down, but if you see others accepting things unthinkingly, That often means there's a better way. After a short break, we'll hear Shelley explain how she took an unconventional route to the CEO suite.

And then operated in an unconventional way. When you've built substantial wealth through your business, it's often tied up in a single equity position. The upside is real, but so is the risk, and knowing when to act isn't always obvious. Creative planning works with business owners to build a strategy around concentrated equity. When to diversify, how to manage tax risk, and how to protect what you've spent years building.

Creative planning where wealth works together. Lear more at creative plating dot com slash masters of scale. Humans will never be more intelligent than AI. There's gonna be two types of companies. Those were great at AI and those that went out of business because they weren't. How do we build a future? That is human centered.

I'm Rana El Calyubi. And on my podcast Pioneers of AI, we answer that question and so many more. As an AI scientist, entrepreneur, and investor, I know what it takes to build AI that works for everyone. Every week I sit down with the pioneers shaping our future. and we take you behind the scenes of the AI that's transforming our lives. Find pioneers of AI wherever you tune in.

Hey there, it's Jill Slessinger. I'm launching a new show. It's called Money Moves, and your money is going to move. We're gonna help you make better financial decisions. We're gonna call out the BS you're finding all over social media. We're gonna give you actionable guidance to make your financial life clearer, less stressful. We're gonna answer your financial questions and take the mystery out of your financial life. Follow and listen to Money Moves with Jill Schlesinger wherever you get your podcast. Before the break, we heard L ofest Sally Krawchek and Callend Lee's Tope Awatona explain how thinking like an outsider propelled their success.

Now Shelley R Shambaux explains how she orchestrated a dynamic turnaround as CEO of a struggling tech firm. By embracing her outsider roots. Then we'll hear lessons about instilling outsider thinking in an organization. Reinforcing the right values and behaviors. And staying confident in the face of criticism.

Let's join back in. Shelley, you have a you have a story for us? I've been an outsider my Entire life. Growing up, we lived in neighborhoods where I was not only the only black girl in my class, but many times in the school.

Other than my family members. And this was the sixties and seventies, a time when for as many people who felt there should be civil rights. You had just as many that didn't. And they let this little black girl know that. So I grew up being frankly bullied.

Verbal abuse, physical abuse. Scott. Pushed down, knocked down, beat up. I mean it was not good. So it was very clear to me. That the odds were in my favor. And when I learned

I had to pay really close attention to what was happening around me. And that was for self preservation. And number two. I learned It's important to do my own research.

Because what people tell me Isn't necessarily in my best interest. So Fast forward, right, on those two things. I get my opportunity.

To be CEO, which as Bob said was something I was absolutely striving for. Vinod Kosla hires me to be CEO of a company called Sablet. Zaplet at the time was Frankly failing. It was failing. We were burning.

A couple million dollars a quarter. This is Two thousand and three. The dot gum bubble had burst, and Zaplet was selling a product, and nobody's interested in this product. So it was clear. That

We needed But the company hadn't realized it yet. It wasn't that we had a broken value proposition. We had no value proposition. So I dusted off what I've learned.

Early on, number one, you look outside. I went and spoke to the smartest people I could find. The question I was asking Is what is a problem you're seeing in corporate America? That's really hard.

Roger McNamy, some may know that name. Roger. Said to me. You know, Shelley, this compliance stuff. It's just killing companies.

I don't know what you do about it, but compliance is a real hard problem. Well I tested off skill number two, which is you always go do your own research. So I did research around compliance with the team, and you know what? It was a big problem and there's huge fines that companies pay. I'm like all right. Now

I have a platform. Because the applet had built a platform. I was just trying to find a problem to solve. So we decided to take that platform and build the apps ourselves. That would solve compliance. We called it comprehensive compliance and risk. And that's what we were gonna take to market. The only problem is I still had no money. So Veno Coslin introduced me to a company called MetricStream. They were a small startup doing

Really quality compliance. We put the two together, took the metric stream name much better than Zapplet when you're trying to sell to CIOs. And that's what we did. And the good news is Over the course of several years we built MetricStream into a global market leader. So Listening to the outside. Thank you, but paying attention, real attention. I tell people

Good advice, good ideas fall from the sky. We just have to be listening for it. Right, just listening for it. I would love to hear about You were

On a glass cliff. you were leading a business probably those who look like the norm of a CEO maybe weren't interested in leading. You just said people didn't know there was a problem. How do you lead and as such a visible outsider and outside leader, how do you lead the organization through that and the people through that pivot. Sure. Pivoting's not easy.

I mean they'd spent Years, right? A few years building this product. They loved this product. And I'm gonna come in and say hey, everything you've done is Kind of.

Worthless? No, that that doesn't work. So what I did was I told him a story, which I'll share with you. Because this is a problem that many startups fall into. Put all your time and effort into this product.

Right? You give the product everything it needs, all the time, the focus, the whole bit. You treat this product kinda like your baby. This is your baby. Well, for those of you who've had a baby or been around babies No one can tell a new parent that their baby is ugly. Nobody.

Right? Oh no, no, you just you just haven't looked at her in the right light. You know, wait wait, you see the face she makes when she burps, right? I mean, no, be a beautiful baby, right? Well the key is Don't fall in love with your product. What you wanna do is fall in love with the market that you're targeting. That's where you want to put all your love, caring, and feeding. You want to meet all their needs, right? All their requirements.

And so coming into Sablet, it was basically sharing the story of, listen, yes, you've burnt the baby and that's Wonderful. But That's not the actual baby you were trying to birth. The baby you're trying to birth is the problem that you're trying to solve for all these people. So let's understand them, what they need and what they require. And take everything we've done.

And just Morph it to meet Their needs. So helping them, we have to give the inspiration the picture so that they feel good about what they've done. but want to work towards where they need to go.

I'm curious, all three of you have uh backgrounds and legacies as outsiders when you're running a team Not everyone on your team has that history, right? But you wanna instill that kind of outsider thinking into The way they operate. Are there Tips or suggestions or experience that you could share with this group, share with each other about how you get a team to have outsider thinking when maybe it's a very important thing.

That's not the place that they start from. It's how to me it's how you ask the questions. So in leadership meetings when you're pulling people together Yeah, that's the question. So somebody share, what's the newest thing you've learned in the in the field right now? You just start asking questions that are actually outside in.

Once you do that and people realize you're gonna continue to do it, guess what? They're gonna go find those answers so they have something to say, right, during that conversation. But I find if you ask the right questions and just make it consistent People realize that's part of what they're supposed to do.

One of the things we do is we have core values, right? That really reflect that outsider thinking. And a lot of companies have core values. We're not unique in that. I think what we try to do differently is really live by those core values. So two core values that came up from our origin story are one. Find a way, which is really about being resourceful and being scrappy. And we reward that, right? So it's not just the value that we have on our website. We have awards for that. We recognize that in the work that people do to reinforce that behavior. And then the other one we have is uh start with human, which is really about

human centricity in the decisions that we make. You know, I as a CEO can single handedly just write these uh values on a tablet and just post them out on a on a wall. There's actually a process in which we said, Hey, let's take a look at why we've gotten here. What are the things we like about the way we've gotten here, what are the things we don't like, and what is the uh way we aspired to be. It's a combination of really making sure that you're intentional and deliberate in the creation of those values and then beginning to assess people against that and allowing people to self select into that system. one of the really great things about startups is You get to decide.

You know, who works there? Whereas our industry is eighty percent men. Bellevis were eighty percent women were fifty percent people of color. And so what we did is we brought the outsiders in. We brought in certainly people who have fintech and financial services experience, but our first head of product came to us from White Watchers, who was an expert in Behavior change in women.

And so we said let's bring these folks in reflect. the client the customer back to her And so we're several steps ahead as we're building the product, understanding what her needs are, because we are her. But it is it's it's interesting. For some of you it it's about the people. And to some extent

It's as you're talking about, Shelly, it's it's a little bit about the process about how you get those people to think a little differently. It's that it's that interplay, but Oh it's it's absolutely both. Because Behavior you want, you won't consistently get as a leader unless you are to Tope's point. Reinforcing it.

Right, every day with other things that you do. But then you have to build it into just process and how people do their jobs, so it just becomes second nature and not an exercise. Exercises don't last. They don't scale, they don't last. You have to figure out how to build it in to how the company actually operates.

I just wanna acknowledge that sometimes being the outsider I mean in settings like this it's like everyone's cheering but it It's also hard when you are the one that is The renegade. Whether you're that within your industry, whether you're that within your team, like as managers we always oh we love having that renegade there, but you know that renegade isn't always the one who moves up. And look, sometimes it's sort of tough to stick out and people Have points of view on you.

That are based on what's going on with them, not with you. So When I did my last race, someone Well, we're not gonna invest in her because we heard she was a bitch. And I'm like And

But you end up they they end up being stereotypes about you when you are One of the few. I think you just have to embrace that outsider status. I think it is indeed harder, but I think all great things are m by definition difficult. But I absolutely enjoy being a contrarian. I get a lot of pleasure in it.

And yeah, just embrace it. Shelley, final thought? Final thought here is It can be hard at times. Absolutely. Especially when people are telling you you should be doing A and you know you should be doing B. But just remember

Nobody knows you or the company better than you do as the leader. Nobody. So all the rest of this are just thoughts and ideas. Think about them. But be confident in yourself and what you believe. Because you've got the depth.

You've got to depth. So just move forward. Well. Terrific. Thank you. Shelley and Tope and Sally, thanks so much.

Listening to Tope Shelley and Sally, I'm struck by their confidence. Thinking like an outsider may sound romantic, but it takes courage and conviction. The models of success that are around us can be restricting. To find a new better way we have to think in a different way. And do so consistently and intentionally.

And when we do Anything's possible. I'm Bob Safian, thanks for listening. Hey listeners, Bob here. If you listen to Rapid Response on Masters of Scale, you may be missing half the show. Because every Friday we release a second rapid response exclusively in the Rapid Response feed. The guests and topics are just as compelling and timely from Ford's CEO to NASA's administrator to the lessons from The Devil Wears Prada. It takes about

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