How to Pitch Millennial Investors

John Livesay interviews Lee Caraher

Hi, and welcome to The Successful Pitch. Today’s guest is Lee Caraher, who wrote a wonderful book called Millennials & Management: The Essential Guide to Making it Work at Work. Lee has over 20 years’ experience in Silicon Valley, producing integrated work teams that get a great deal done and have fun at the same time. She’s known as a communication strategist for practical solutions to the big problems. She founded Double Forte in 2002 to work with good people doing great work for good companies. Her clients span from well-loved brands and high tech startups not only in the San Francisco Bay Area, but Boston, New York, and even Europe. She struggled with trying to figure out how to work well with the millennial clients, and more than half of her own staff is under 32. She wrote this book saying, “I was fed up with the negative stereotypes that millennials are burdened with that they’re determined to figure out how to create a culture where boomers, and Gen X-ers, and millennials can all thrive together.” Lee, welcome to the show.

John, it is so great to be with you. Thank you so much for having me.

I love people who have fun at work, have high energy, and like to solve problems, because that’s the key to get funded. What problem do you solve and is it a big enough problem that I could get a big enough return on my investment, right?


That’s what our audience loves to hear. But, before we get into how you started Double Forte — obviously you’re an entrepreneur yourself — take us back to your experience in being an entrepreneur before.

Before Double Forte, I worked for Interpublic, a very large multinational media firm, and before that, I was at SEGA of America, the video game company, when SEGA of America was a $1.5 billion company. I left SEGA to go to Interpublic Companies in the dotcom boom, and I worked with, I can’t even count how many startups, and took more than 20 public. Then, the boom crashed.
In 2001, around 9/11 was a big moment in my life when I decided that I didn’t want to be in the big firm anymore. I really wanted to be able to craft what was important to me and create that workplace that meant that I was doing what I wanted to do more than flying around the country and waving my magic wand. I had 750 people when I was in that company. They were very, very generous to me, but 9/11 really crystallized that wasn’t for me; it was for somebody else. My intention was actually to take a whole year off.
I had two young children, I went to yoga, I organized my house — all this stuff. I’m the chief bacon officer in my house. My husband is the chief home officer — that’s what we call each other — and I basically drove my husband crazy. With the color coding and the flower arranging and three glue guns, I was just destructive. I drove my husband crazy and he’s like, “We’re not going to make it if you don’t use your time outside of the house.”
I have always been very intrapreneurial. I started two companies for Interpublic Company, and at SEGA, I did all this intrapreneurial stuff as well. I was pretty risk-averse. Then, in 2002, it was clear that I needed to go back to work. I wasn’t going to last a year glue gunning everything, that’s for sure. I am the breadwinner and we had all these unexpected expenses and I was looking for jobs. I was in the running for two very big jobs and then my mother got sick. I live in San Francisco and my parents lived in Wisconsin and my mother got sick. She got diagnosed with four months to live and it was very clear that I was going to be with her.
I withdrew and I couldn’t take either of the jobs because I was going to go be with my mom when she needed it. Out of necessity, I created my company because I had to bring home the bacon and I had to be in Wisconsin, and my home is in San Francisco. In my kind of work, when you’re in-house, you don’t really have the freedom to be wherever you want to be, even in today’s world. So, I decided that I really like this job that I do. I didn’t like how it gets expressed in a large, publicly traded media company, but I love what we do. Figuring out what to say and who to say it to, and helping people really understand their story and how to convey it. Because, people aren’t really good at it.
I feel like when you’re really close to an idea, it’s harder, and harder, and harder to explain it to someone who’s not close to it. That’s when I decided to start Double Forte, and here we are 13 years later, and I guess I’m now fully fledged entrepreneurial. Because, when you’re an entrepreneur, what you start and what you are in are probably two very different things. A plan is wonderful, but really, the goal is more important.

I like that.

Plans should be in sand, but goals need to be in concrete. Then, you react to or respond to what the conditions are. We have probably reinvented ourselves four times since we started in 2002 to respond to the economy, to what the world’s doing in communication, to the competitive situation and to who we want to serve. We’re going to be 14 in a few months. I’m not sure I thought that when I started, but here we are, and it’s new every day, which is what keeps me interested.

“A plan is in sand, but goals should be in concrete.” That’s a great line. That’s really helpful. Well, let’s take a little deeper dive into what you said earlier, because you’re such a master storyteller in crafting something, especially if it’s techy. You do it for the media, but the same skills apply for crafting a pitch for investors. Do you have any tips on how to take something that’s fairly complicated or techy? How do you craft that for the media?

I think the most important thing in crafting your story is to frame your story with a problem, and to describe the problem and the scale of the problem quickly up front, and then to explain. #1: what’s the problem, what’s the scale of that problem? #2: what is your inspiration to solve that problem? #3: what is your approach to solve that problem and how does it differ from what’s in the marketplace today?
If you can be very clear that this is a problem and it’s big. It’s worth so many dollars, number one. Number two, that you have a passion to solve it and why you were inspired to do it. I think investors are looking for people who are smart, who are business-savvy, but who are just compelled to do something to get it done, and they have a big passion for that problem they’re solving. At least good money, right?
In an investment, there’s bad money and there’s good money. It’s all money, it’s all dollars, but bad money, from my perspective, is money that is just for that quick ROI, it’s not really there to serve and help you get there. Not a connector, not help, but mostly just criticizing and diverting you from the goal and saying, “That wasn’t your plan.” I’ve never seen a plan that executed 100% ever in my career because you just can’t control everything. The purpose of a plan is to know where you should be so you can try and get it back to the point.
But, in my experience, good money is from people who support the passion and the brains of the founders. There should be some dollars there. Why are you inspired to solve this problem? How are you going to do it? What’s the innovation? Scale comes in innovation, not necessarily in just getting more efficiency. Scale comes in innovation and investors are looking for innovation and scale to get their ROI out in a productive way.

‘Scale comes in innovation, not efficiency.’ I love that. It’s all about, yes, finding the good money that supports the passion of the founder, and then that goes to the whole point of whether you’re creating a team of people to work with you or investors, they all need to fit into the same culture. That’s the perfect segue into your expertise around millennials. Let’s just define for everybody exactly how old millennials are right now.

Millennials in 2016 will turn 16 to 36. It’s 20 years. It’s a big band, right? I break them down into three sections. The first section is the oldest section: 28-year-olds to 36-year-olds, and these people came into the marketplace after 9/11. As adults, they’ve never been to the gate to pick up a family member or a girlfriend, or a boyfriend or a friend. They’ve never done that at the airport. They are used to giving their IDs to get into a building. Their idea of privacy and security is very different from their older colleagues.
The next group is probably 23-28, and these people came into the workplace after 2008, 2009, and this is the group that’s had the toughest time finding work commence with their education. There are still millennials looking and trying to catch up to where they thought they should be, given their education and the economy.
The third group is 16-22. People who are in school, high school-ers and college students. This group of people learned entirely different from that oldest group. The iPad did not exist for the oldest group, and now schools have iPads for every kid and they’re looking at videos at night and doing their homework in the classroom during the day. They learn very differently. They’ve had very different kinds of technologies. The whole generation definitely benefits from being technology-savant, for sure. They’re digitally native, they all benefit from that. The youngest group is probably going to benefit from it the most.

It’s so funny because, in business, really, luxury, high-end and really low-end companies do well, and it’s that middle ground that’s tricky. Same thing with restaurants. Fast food or really expensive restaurants do well, and then that middle ground always seems to struggle the most. The same thing is true the way you broke up this millennial age group that that middle ground is struggling to get where they need to be. I’m fascinated. I never thought of it as the 28 to 36-year-olds never dropped people off at the airport and all that stuff because of 9/11, right?


You just get yourself there and don’t wait in line to pick someone up, and it doesn’t mean that they don’t love them, it’s just that they’re going to consider it, right?

There was a time, in some airports around the country, that you couldn’t even get to the airport unless you showed your boarding pass. But they definitely have never been to the gate, have never gone through security to get to the gate to say goodbye at the gate, or welcome someone at the gate ever.

You told me before we started this show, that you spoke at the White House about this. Tell me about that experience. How did that come about?

They called me.

Did you think it was a prank call?

I did. I thought it was a prank call, so I said, “I’m very happy to talk with you. I’m on my way to a meeting. If you can email with what you need and what the dates are, I will be happy to call you back,” and sure enough, an email came through at I was doing a keynote in D.C. about millennials in the government, and I think some of their people were there. They had seen the roster and they invited me to come. It was an amazing experience. That is a dedicated group of people. No matter where you are on the political spectrum, the people who are in the White House working every day for us are doing tremendous work. I just gave a workshop, mostly about interns — they have over 150 interns at a time — and how to productively work with interns so that everybody benefits.
No matter where you are — it has nothing to do with the White House — a lot of companies start with interns to try them out before they buy them, you know? Not the White House. The White House works very differently. Interns often show up into the business world just ready to go in that business pitch with you, like, “Well, you know, first we need to change your wardrobe and then you don’t get to go to the top sales guy day 1 kind of stuff.”
There’s a lot of false expectations that have been set by the media, by parents, and by education about what an internship’s all about. I have lots of stories in my book about interns, and interns are the life blood of the future. Millennials who are getting out of college are super smart, super capable, have a lot of energy, and want to matter. You have to figure out a way for interns to matter and not drop down into your boss’s desk and say, “Hey, what’s going on?” because that is normal, that happens all the time. How I work with companies who use interns is helping them set expectations before they show up and explain what you’re going to get out of being an intern in the company.

Now, you’ve been called the ‘Millennial Whisperer’. How did you get that title?

My friend called me that and tweeted it out. She goes, “Lee is the Millennial Whisperer,” and I was like, “Oh, my gosh. That’s a little pretentious. I can’t call myself that.” But, then all of a sudden, all my friends would call me and say, “Okay, we have this millennial, I have a problem with him. I don’t know what to do,” and I would help them figure it out, sort of like the Dog Whisperer, I guess. Cesar, right?

Right. I love it.

It just picked up from there. I prefer the ‘Millennial Champion’, because my book came about because I failed miserably at hiring and keeping millennials. My company hired six millennials within about eight weeks of each other and they all were gone within three months. One person could be their problem, two people, maybe, but all six at the same time, that had to be us. When I started looking into it, I didn’t know there was such a thing as a millennial at the time. It was all negative; it’s so negative, and I just can’t be negative every day.
An entrepreneur is an optimistic person. An entrepreneur believes that they have a future that they can make things happen. I’m an optimistic person. Frankly, if you don’t have millennials in your business, you don’t have a future in your business.
But wait, there’s more!?

This post has been adapted from The Successful Pitch podcast. Listen to this past episode for more on the inspiring story of Lee Caraher

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As a funding strategist, John Livesay helps CEOs craft a compelling pitch which engages investors in a way that inspires them to join a startup’s team.

After a successful 20-year career in media sales with Conde Nast where he worked across all 22 brands in their corporate division [GQ, Vanity Fair, Wired, W and Vogue] and created integrated programs for clients such as Lexus, Hyundai and Guess, John won salesperson of the year in 2012 across the entire company.

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