Pitching, Pricing, and Small Wins

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My Guest: Angie Hicks, co-founder of Angie's List (now called Angi). She started the company at just 23, going door-to-door as a self-described introvert and non-salesperson, and turned it into a national platform trusted by millions. During our conversation, we discuss what it takes to lead with authenticity and build lasting impact.

Key Learnings

Lead by listening and showing up. Whether it's knocking on doors as a 23-year-old or meeting employees during office hours as CEO, Angie reminds us that being present, paying attention, and seeking feedback is the heart of leadership.

Focus on people and learning. Angie's career filter is simple: Do I like the people I'm working with? Am I learning new things? If yes, keep going. If not, it's time to reconsider. Excellence isn't just about results. It's about the environment and growth around you.

Take your work seriously, but not yourself. Confidence, humility, and authenticity go hand in hand. Angie shows us that you can be ambitious and driven without losing sight of the human side of leadership.

From Angie...

My co-founder, Bill Osterle, came to me when I was a senior in college and said, "Hey, I've got a crazy idea. Your parents are gonna hate it. But why don't we start a business?" I talked to my parents, talked to my friends, and then I ended up talking to my grandfather who was incredibly conservative. He grew up in the Depression, very fiscally responsible.

"What do you have to lose? You're 22, your parents aren't going to let you starve, and you're not trying to support a family, so why don't you try it?"

I was so taken aback by his response that that comment was probably what pushed me over the edge. I think young people can do this a lot, as we tend to overthink decisions. Sometimes people see things in you that you don't see in yourself, and you've gotta have a little faith. What better time to have a little faith than when you're young and carefree?

Work hard, and things will come your way.

We started in 1995. It was an offline world. We started as a call-in service and a monthly newsletter. The first name of the company was Columbus Neighbors. We left it like that for a year, and people just didn't get it. They thought the newsletter was the list. We decided to do a rebranding nine months in. We had two options: The List or Jackie's List (Jackie was the mother of one of our investors who knew everybody). At the last minute, Bill said maybe it should be Angie's List. "She does answer the phone."

Going door to door was hard. There was a lot of crying, I will be honest. I was selling something that wasn't concrete. "Hey, so when you need a plumber, you're gonna call me and I'm gonna help you find a plumber. And then when you hire someone, you're gonna tell me about it." I viewed it as a numbers game. I need to knock on so many doors every day, and that's just what I'm going to do. Hopefully, if I stay on my pitch and I knock on enough doors, I will sell the right number of memberships. If I was selling one or two memberships a day, that's great. No business was gonna be built on me selling one or two memberships a day, but that's where we were.

Sometimes you have to do the hard stuff. Sometimes you have to do the stuff you're not good at, and you have to figure out ways to work around it.

Because no matter what you do in your career, there's gonna be stuff you don't love. I broke it down by like, I'm gonna do it for these two hours. I'm a believer in the you can do anything for a year philosophy. I could do anything for an hour a day. So you have to kind of disconnect and treat it that way, as this is like taking my medicine. But you do win every once in a while. And it is fun when you win. It is fun when you sell something. The day Patty gave me her church directory was the best day ever.

You gotta celebrate the little wins as well in life.

Starting a business is a long journey. It is more of a marathon than a sprint. There's usually not this burst of momentum where everything rolls your way. It's building blocks along the way. If you don't celebrate those little wins and you only focus on, oh, I'm not gonna be happy until we're at 10,000 members, that could be years. You need things to keep you going every day.

Patty lived near Bill, so she kinda liked him too, but I think there was a little bit of entrepreneur in Patty. Patty needed nothing from us. She had lived in Columbus her entire life. She had renovated a 1920s house. All she was able to do was give. She knew everybody. But I think she just loved the spirit.

You don't know whether that's door seven, door one, door 57, you don't know.

But there is typically a breakthrough. Staying true and persistent, you know, there probably weren't a lot of women starting businesses going door to door in 1995, and Patty was like, look, she's got some gumption. She's tackling a business that in many ways is a man's world. Construction is a man's world.

Whether that's starting a business or finding the right boss, or finding the right position, that same lesson is the same. I talk to young people, I say, Hey, you can do marketing anywhere. There's any company you can do marketing. When it comes to me... Go where you're gonna be with somebody who believes in you. That's gonna invest in you, because that's actually what's gonna change your trajectory.

It's not the name on the company that's gonna change your trajectory. It's actually who's got your back, who's coaching you, that's going to make the biggest difference.

The next inflection point for me was when we opened in Cleveland the year after that. It was the first market we had opened from scratch. I remember I went one morning and picked up the newspaper, picked up the Plain Dealer at the bagel shop across the street from my office. And there it was, our little two-by-three ad that said, "Tired of lousy service" with some clip art. I was so excited. I was like, This is amazing. We're in Cleveland. This is gonna be so great. And then I remember telling Bill, "We're gonna get so many calls." And he's like, "We're gonna get so many calls." And I don't think we got any calls that day.

The transition from individual contributor to leading others was a horrible transition. It's actually really hard. I tell people that all the time because if you think about who do we promote in companies, we promote really strong individual performers.

The skills that make us really good individual performers do not necessarily make us good leaders, managers, et cetera, because it's actually a whole different skillset.

I was that overachiever kind of controller, let me just do it type person. You have to actually train yourself to not do those things because no one's ever going to be successful and learn if you're just over there stepping in. The early days when I was young and trying to manage people, not good. Not good at all. I ended up leaving for a year and a half to go to business school. I was pretty burnt out on the business, and I probably would've left the business had I not gone. It gave me a chance to reflect on where I've been and step back. Now I understand, I'm not in the pressure cooker. I can see where I've mistepped.

I left when I was 25, three years in. The business had gotten big enoug,h and we decided to bring in a CEO because the 22- 23-year-old was kinda like, maybe we need some leadership here. My co-founder joined full-time at that point and came in as CEO. I joke around, I'm like, take a break. I was still keeping the books.

The TV commercial was a hundred thousand dollars, which I had to convince our board on. I was like, look, either we try this or we just close Cleveland because there is no scenario here that we're gonna build a business with door-to-door sales at the rate we're moving. We basically took everything on Cleveland, which was $100,000. I would've been devastated had it failed. People started calling. I was so excited. Then all of a sudden it just kinda went bananas. You realize there's a lot of people with this problem. Doors slammed in my face at that point, not as much of an issue. And then we ended up being in Boston and Washington, and a bunch of other cities. Every time we'd go to a city, I'd fly in, and I would open the paper, and I would get all happy.

The TV commercials themselves were funny because I can't do anything for fun anymore without seeing myself in the commercial.

I did the first one, and they're like, listen, we're just gonna, we're not gonna tell anybody. It's just gonna go on, you know, we're just gonna do it really quietly. I was like, great. Okay, fine. And then it kind of took off. I had young kids at the time. I wouldn't let us advertise on kids' shows. There was never us on Disney Channel or Nickelodeon because I didn't want that. But the kids would see me on TV. You know, they would see me doing interviews. It happened for them at such a young age that they just kind of thought that's what parents did. I remember one of my kids coming home in middle school and being like, I can't believe you didn't tell me you were famous because it was finally, the friends had grown up enough that they were like, you know who her mom is, right?

I became a little more closed off in my personal life as I became more public. Kids deserve to grow up in a world where they get to be kids and not have to deal with that stuff. In our little town, people were like, Oh yeah, she just lives here. And it became not a thing. It became more relevant to me when I was traveling.

I started doing office hours. I did it on Fridays leading into the lunchtime, which, let's be honest, was probably one of the squishiest times of productive work. I was with a group of CEOs the other day, and I actually suggested, just try a little. It doesn't have to be a big thing. Just try a little and see where it takes you.

The meetings were anything. It was career advice. What should I do? They might have ideas for the business. Hey, we should go into this line. I remember talking one day to our head of legal, and I was like, you know, I don't get open-door media requests anymore. And she kind of chuckled, and she said, That's because you have them all the time.

You allow problems to come to you before they're big problems, so they become less of a thing.

I'd rather people bring their concerns internally first and listen to 'em and address 'em when you can. They always come internally first, whether it's from an employee, whether it's from a customer. It's just how we handle those things as to whether they blow up into something bigger. I always tried to give them something in return. They come to talk to me and I'd introduce 'em to someone who would help. I'd open a door for them.

To this day, I still love talking to customers. I think we live in a very digital age, and I feel like we don't talk to one another very much. People like people. They need to feel heard and have things resolved. I took that office hours idea, and now I do it with customers, so any pro can sign up and talk to me. Gives me a chance to understand, get a pulse on what's going on.

The people on the front line are the ones who are making your brand.

The marketing team might make some great social posts and some great TV ads. But many times, the people who are manning the phones or your chats are the ones that are leaving a more lasting impression on your brand than anything else. How do you bring the voice of the customer into the organization? Not everybody in our company is a homeowner. How do you make sure they can understand the customer? What's life like as a small business owner, as a pro? What's it like for a homeowner when something goes awry on their worst day? How do I bring those stories to life?

I had to convince myself that it was a good use of time. Busy people who have lots of responsibility are active doers, overachievers, to sit back and talk and listen feels like, Okay, am I moving the needle? It feels a bit too squishy. That's why I would treat it just like some of the other things. I will give it an hour a week. Let's see what happens there. I could see the payoff. I can't go spend 30% of my time doing this, but there is a portion of time that I do dedicate.

Feedback is a gift and something you should seek out. But yeah, it doesn't always feel great. One of the hardest pieces of advice I got came at a time when we were actually trying to do a transaction. They said, "You have an executive presence issue." And I was like, what? They said, "You're too nice to everybody. It doesn't help the company." I can't tell you how much that comment just killed me. But then I went out and got an executive coach, and I reflected on it. In many ways, it made me a better CEO. I learned that I could be me and I could still be nice and I could be kind, but there are moments I have to be clear.

When I'm looking to promote someone or hire someone, knowing your stuff is super important. You don't want this person, who says, I'm the one who always knows the answer. You want someone who can learn from their team. I spent most of my career running marketing, and marketing moves fast. Some of the youngest members of the team are teaching me more things over the years than even some of the more seasoned marketing people. How are you constantly having a view about learning and staying smart in the trade?

The ability to just be a good partner or work with people is important.

Your job's not to come in and knock down walls. It's actually to build relationships because you can't do everything yourself. How are you at building cross-department relationships?

My advice to recent grads: One of my favorites, take your work very seriously. Be good at what you do. Don't always be looking for that next thing that you gotta go tackle. Do what's in front of you first.

Don't take yourself too seriously.

You come out, you're like, Oh, I have all of these credentials. I should therefore be able to do these things. Sometimes the envelopes need stuffed and we might all do that together. So don't take yourself too seriously. We're gonna do this together.

Be open to feedback and to helping others. Don't be afraid when people suggest things that seem totally counter. I think sometimes we get too rigid in our plans. I use Angie's List as an example. I was supposed to be a consultant. I was supposed to go be a business consultant, but then Bill comes in and says, hey, what about this? I could have easily been a business consultant and had a nice life. But I chose that door. A lot of times, people get a little too narrow in their focus and miss opportunities. So stay open to that.

For me, it's all about the people you work with.

Working with people that you're learning from, that believe in you, that's all that matters. I overindex there. People ask me, how are you still doing this after 30 years? I ask myself two questions, and if I can answer yes to those two questions, I'm in. If I answer no, I'm out.

The two things are: Do I like the people I'm working with, and am I learning new things?

When you're as long in your career as I am, you have to dedicate time and effort to learning new things so that you don't become that person that is like, we do this because we've always done it this way. Which I think is just like the worst line ever.

1. Angie's grandfather asked, "What do you have to lose?" when she was 22 and hesitating about starting a business. What decision are you currently overthinking that you might need to just take a leap on while you're young (or young enough) and the risk is manageable? S
2. She says the skills that make us really good individual performers don't necessarily make us good leaders. If you've recently been promoted or are leading others, what specific "doer" habits do you need to let go of so your team can learn and succeed?
3. Angie stayed at Angi for 30 years by asking herself two questions: "Do I like the people I'm working with?" and "Am I learning new things?" How would you honestly answer those two questions about your current role? If the answer to either is no, what does that tell you?