Unapologetically Ambitious: Entrepreneur and Former CEO Shellye Archambeau Joins Startup Savants

This episode of Startup Savants features Shelleye Archambeau, an entrepreneur, a former IBM sales executive, and a former CEO of Blockbuster Video. She joins Startup Savants to share the wisdom she has gleaned throughout her career and discuss her new book, Unapologetically Ambitious.

Talking with podcast hosts Annaka and Ethan, Shelleye details her impressive business career and the valuable lessons she has learned along the way that can apply to any entrepreneur. She also shares wisdom from her book, which explains how to get what you want out of life — both personally and professionally.

What is your book about and why is it important that you wrote it?

“The book is really about how to get what you want out of life, professionally and personally, by improving your odds every step of the way. I wrote the book because early on, I tried to be really accessible. There aren’t many black women in technology doing the things that I’ve done, and therefore I wanted people to be able to touch me. If they touch me, they realize, ‘Hey, I’m a real person. If I can do it, you can do it.’

But as I got more and more responsibility, I couldn’t actually meet with everybody. I still responded to email, texts, whatever. But I said, ‘You know what? When I get to phase two, I’m going to write it down. I’m going to write down what worked, what didn’t, and talk about it’ … and that’s why I wrote the book because I just wanted to share what I never saw, which was a book that really talked about life holistically.”

What would you say is the biggest takeaway that you want readers to have when they finish your book?

“I wanted them to walk away with the perspective that if they’re intentional about what they want to do if they set goals, and really are intentional about the steps they take to get there, that they really can improve their odds. A lot of people set goals, and some people think about plans for their goals, but very few people make decisions every day consistent with what they’re actually trying to do. And that’s where the power lies. So I wanted people to take away, ‘I don’t have to do everything Shelley did.’ That was not the objective. The objective was just to share that if you are intentional and strategic about each step, you can actually improve your odds and get what you want ultimately.”

Can you walk us through your career and how you got to where you are today?

“It was really in high school that I decided that I wanted to be a CEO. Not because I knew what a CEO was, frankly, but because I had a guidance counselor who [noted] that I liked working in clubs and leading clubs and that clubs were like business. And I said, ‘Oh, okay, well, I like to lead clubs. So I’ll go lead a business.’ And when I looked up, those people were called CEOs. So I said, ‘I’m going to go be a CEO.’ Audacious and ignorant, I had no clue what that really meant. But I did know that I needed to do some research to figure it out.

I knew I needed credentials, so I went to Wharton. I wanted to be in tech because it was a growing industry. And I heard along the way that those industries have the best opportunities. So I decided to join IBM. And the research showed that every CEO of IBM started out in sales. So despite the fact that people thought I was crazy coming out of Wharton and going to sell computers, that’s what I did because I figured that was a path to power. And I rose through my sales career into management, general management, vice president, running multibillion-dollar divisions at IBM, then got to the point where my boss reported to the CEO, and I wasn’t really getting all the signs that told me that I was going to have an opportunity to compete for the CEO role. So I worked my way to Silicon Valley. 

I left IBM, a very tough decision to become president of Blockbuster.com … back in the late 90s. Back then, Blockbuster was a behemoth everywhere … and unfortunately, Blockbuster didn’t really have the vision for where things were going. And so, I decided, you know what I need to get where everything is really happening, and that was Silicon Valley. So I moved to Silicon Valley to take the chief marketing officer and VP of sales roles at two public companies before I ultimately went after my CEO role at what became MetricStream. And I ran that for 15 years before passing the CEO baton.”

Do you see a sales job as being the perfect first job for anyone, or just for specific people?

“I think it’s the best first job for anyone. I don’t care if it’s a part-time job selling something while you’re in school or a full-time job when you come out of school – what sales does for you is you learn so much. The first thing you learn is courage because you can’t sell anything unless you ask for the order. And that takes courage.

Two, you learn that no doesn’t mean no. No just means something’s not right. So either the timing’s not right, the funding’s not right, the value proposition’s not right, the decision-making … Something is not right. So getting a no is great because it gives you a chance to find out what’s wrong. So much better to ask for what it is that you want and get a no, so that you can follow up on it than to not know what it is that’s actually holding you back. And then you learn how to power in rooms, how to read people, you learn how to connect and build trust and confidence. You learn how to actually communicate and package what it is that you’re trying to sell in a way in which people will understand and appreciate. So learning it early, I think it just gives you a big head start.”

Throughout your time at IBM, you found out how the power flows through a company to move yourself closer to your final goal of being the CEO. Can you give us the definition of the flow of power?

“Staying close to how the company makes money tends to be a current or power of flow.

But every company is different. What you want to do is to look to see how people are moving through the company. People who become directors and vice presidents and general managers and presidents and whatever, what are their roles? What organizations are they in? You tend to find [that] 70% of the people have done it through [a certain] kind of path. I call that the current. It doesn’t mean you can’t get there without being on the current, but I find if you actually get onto the current of power, you can move farther more quickly.”

How would you tell an entrepreneur of a scaling company how to identify the flow to achieve that success or to move into that position that they would like to move themselves into?

When you’re a founder of a business, the flow you’re trying to find is not the flow within your company, but you’re trying to find the flow within the target industry or segment in which you are operating. And so the key there is to really spend time understanding who your target market is. Who are they? What do they like? Where do they spend time? What are the different periodicals, podcasts? Where do they get their information? What kinds of backgrounds do they come from? And the reason you want to know all that is it’ll tell you where you need to position yourself to actually get into the current.

So you can find the current by understanding your target market better than anybody else and putting yourself in their way, putting yourself where they go, where they spend time, where they are looking for information. So the current works, whether it’s an established one within your company, because it’s a big company or in a startup looking for the current within that industry segment that you’re targeting.”

When you become a CEO, you guided your company through the 2008 recession. How do you recommend other founders navigate uncertain times?

“Whenever you’re facing an uncertain time, cash becomes very important because so many companies go out of business. Not because they don’t have a good product, not because they don’t have a good idea, not because they don’t have great customer prospects, it’s because they flat out run out of money. So cash [is] number one.

Number two, I’ve found that things are never as bad as they appear, and they’re also never as good as they appear. So realize it’s just a situation you have to deal with. And as the leader, you want to make sure that you stay pretty calm … because the rest of the company is looking to you to determine how they should feel … You have to model the behavior that you want to see.”

When you’re making huge decisions for your company, who do you go to for feedback?

“It depends upon the decision, but it really comes down to people within the organization and people outside of the organization. I think it’s important to have a set of people who are independent, aren’t drinking the Kool-Aid of your company, that you can bounce ideas off of, and that’s really important. 

But the other thing is, as a leader, you also don’t want to be making all the decisions. If you’re making all the decisions, you’re doing it wrong. You want to make decisions when the team can’t, right? Or when it appears that the team either has a wrong set of assumptions or something that’s leading them in a direction that you just fundamentally do not agree with. But in general, if you’re making all the decisions, then you’re doing something wrong because the number one job of a leader is to build and create more leaders, and you can’t create leaders if you’re making all the decisions. And if you can’t create more leaders, then you can’t scale the company because you become the bottleneck to growth.”

How does a founder get in the right mindset to properly delegate tasks to other people on the team?

“If you’re not spending a good chunk of your time on strategy, on building external relationships and connections tied to the success of your company and your business, then you’re not doing your job. And so what happens is you shouldn’t have enough time to do all of the detailed work if you’re indeed leading and managing your people properly, meaning setting objectives, making sure you are speaking, and doing the external stuff. So I find the best way to do it is that way, look at how I am spending my time.”

What are your thoughts on asking for help?

“I believe that asking for help is a strength, it is not a weakness. There is no one on this planet that has done anything of significance all by themselves. No one. So don’t think you’re going to be the first one to do it. Therefore, ask for help. 

I find if you ask for help, it does a number of things. One, most people who have been asked in the right way are actually willing to be helpful. Number two, asking for help shows that you are vulnerable … It allows people to relate to you. And then third, you actually get help, which means you’re actually able to take advantage of what you’re getting and improve things.”

I want a mentor – what do I need to do to make that happen?

“First of all, what I find is don’t actually ask somebody to be your mentor … It gives them the opportunity to say no, right? Just start treating them like a mentor. Start easy. You wouldn’t come to me and say, ‘Oh Shellye, do you have a second? What should I do with my career?’ That’s not a second. That I have no clue. I don’t know you well enough, that doesn’t get you anywhere. But what you could do is say, ‘Hey Shellye, you just wrote a book. I’m thinking about writing a book, what would be your two pieces of advice?’ Those will probably be top-of-mind things because I just did it, he knows. So I can answer without even investing. 

Now here’s the key: When you ask for that advice, take it and then report back. ‘Shellye, thanks so much for the advice. I now have my first draft, blah, blah, blah.’ Whatever it might be. Now, why do you do that? Because I may not even remember the conversation … But by saying thank you, it’s like, ‘Oh wait, wow, I really had an impact on Ethan.’ It makes me feel good. They won’t remember what you say, they won’t remember what you do, but they’ll remember how you made them feel … and that starts this relationship.”

How can the mentee get the most out of that relationship?

“Remember you own the relationship, not the mentor. And the best way to get the most out of it once you’ve established the relationship and you’ve got to a cadence in a conversation is to be respectful of the mentor’s time. Which means if I reach out to say, ‘Ethan, do you have 15 minutes?’ Tell them why you need the 15 minutes … and be on time. You set the introduction and the calendar invite, you do the work around it to make it easy for the mentor. Give them a chance to think about the topic before you actually get together as an example. And then, like I said, it’s closing the loop. So all of the weight really sits with the mentee because it’s the mentee that’s getting the most value.”

How did the impostor syndrome manifest itself in your career?

“I have suffered from imposter syndrome my entire life, entire life. I still do from time to time, which is absolutely ridiculous … So imposter syndrome is that little voice that when you’re getting ready to face something new, a new job, you’re asked to speak, you join a new group, whatever it means, that little voice that says, ‘What makes you think you are capable of doing this? Wait till they figure out you don’t know as much as they think you know.’ It’s that little voice that is basically reverberating in your brain, all of your worst fears, concerns, self-doubt, the whole bit. And it’s so freaking loud, that voice. That’s imposter syndrome.

Most people suffer from imposter syndrome at some point or another. Women more so than men and actually women of color the most. But frankly, if just about everybody is suffering from it, it means it’s not you, right? It’s kind of in the air … It comes across the airwaves, you watch something, you get scared. What do you do? You turn the thing off. That voice in your head, turn the thing off. 

And if that doesn’t work, remember the only times you really feel it is when you are facing something new. Well, guess what? They wouldn’t be giving you the new opportunity if they didn’t believe in you. So if you can’t believe in yourself, believe them, right? And then, if that doesn’t work, fake the confidence. Act like you know what you’re doing because eventually, if you really think about it, you always figure it out. You always figure it out. And if that doesn’t work, then … get your posse around … We all need people in our lives that rally us forward, which is why you have cheerleaders.”

How do you differentiate between impostor syndrome and ordinary self-doubt?

“Imposter syndrome is when you have that doubt that’s nagging at you, that you just don’t belong, that you really shouldn’t be here, but it typically is not manifested in terms of actually doing things. When you actually get the role, get the job, get whatever it might be, you can do it. It’s just as you’re getting ready to take it on or as you’re getting started, you’re feeling this doubt. But if you’re actually in something and you literally don’t know how to do it [or] where to go for help, then you might be over your head.”

One of the most common roadblocks you see founders running into is falling in love with their product. What’s the danger of that?

“The danger of falling in love with your product is really similar to falling in love with your baby. You know your baby is perfect. You know your baby is beautiful. And people might come over and start making little criticisms or something and they don’t think your baby’s so pretty. And you’re like, ‘Wait, you just haven’t seen her in the right light. Let us tickle it a little bit. Look how she gurgles, right?’ It doesn’t matter what people say, you are not listening because you know your baby is perfect. 

Well, when you’re a founder … it’s almost the same thing. You’ve put your heart and soul into this product. It is perfect … When you fall in love with your product, it really tends to shut your mind and your eyes to external [input]. And that is the death of a product. You don’t want to fall in love with your product. What you want to do is fall in love with your target market … If you’re focused on falling in love with your target market, then all of the energies that you bring in your company will be all about how do I satisfy them the best? And when you do that, then you win.”