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Entrepreneurial Leadership: Growing Yourself Before Growing Your Business with Catherine Dennig · The Growth Class with Phil Masiello

• 0:20
  SPEAKER_01: Hey everybody and welcome back to the growth class.
• 0:22
  SPEAKER_01: It's me, Phil Mastiello, again, your host.
• 0:25
  SPEAKER_01: I'm thrilled to be joined by Catherine Denning, the CEO and co-founder of First Shure.
• 0:31
  SPEAKER_01: But I think that she's actually sold it, but we're going to talk to her about that whole piece.
• 0:36
  SPEAKER_01: But she's a Forbes 30 under 30 honoree and a former senior product manager at Facebook.
• 0:42
  SPEAKER_01: She uh was driven by a personal mission to ensure that no pet owner has to face a heartbreaking financial decision when their animal needs care.
• 0:50
  SPEAKER_01: So she co-founded FurSure in 2020.
• 0:54
  SPEAKER_01: Since its inception, Catherine has scaled the company into a leading fintech marketplace for pet insurance, successfully securing millions in venture funding, which is not an easy thing to do.
• 1:04
  SPEAKER_01: Beyond her work in the pet tech space, she is an expert in remote team management and ruthless prioritization, framework she uses to keep her team focused on measurable results.
• 1:13
  SPEAKER_01: So today we're going to dive into how she turned her personal struggle into a high-growth startup, how she navigates the complexities of the insure tech landscape and the strategies she used to maintain operational excellence while scanning, and anything else, scaling, and anything else she wants to talk about while she's here.
• 1:29
  SPEAKER_01: So let's uh let's bring her in and let's talk to her.
• 1:32
  SPEAKER_01: And how are you doing, Catherine?
• 1:36
  SPEAKER_00: Thanks for taking the time.
• 1:38
  SPEAKER_01: Thanks for taking the time to come on.
• 1:40
  SPEAKER_01: Yeah.
• 1:41
  SPEAKER_03: Thanks for having me.
• 1:42
  SPEAKER_03: Excited.
• 1:44
  SPEAKER_01: Why don't you take us back a little bit about give us a little bit about your history, what you've done, and uh how you got to where you are.
• 1:52
  SPEAKER_03: Yeah.
• 1:53
  SPEAKER_03: I went to Princeton, which is where I'm at my co-founder.
• 1:57
  SPEAKER_03: I didn't know it at the time, uh, but he was a smart person who I respected and we just went about our journeys together.
• 2:05
  SPEAKER_03: And after college, I got the best job that I could get out of college, which was working at Facebook as a senior or as a product manager.
• 2:12
  SPEAKER_03: I did a rotational program.
• 2:13
  SPEAKER_03: Uh and then over the three and a half years that I worked there, I became a senior product manager and um was promoted a few times while I was there.
• 2:21
  SPEAKER_03: And I actually just got really good growth training like out of Facebook since they had two billion users.
• 2:27
  SPEAKER_03: They were really good at growth, not just on the uh individual user side, but also on the businesses side, on the ad side.
• 2:34
  SPEAKER_03: So I worked on the ads growth team.
• 2:36
  SPEAKER_03: And I quit in uh at the end of 2018, at the very end.
• 2:41
  SPEAKER_03: So I had all of 2019 that I told myself I had no idea, no co-founder, and I was just gonna start something that I was passionate about.
• 2:49
  SPEAKER_03: And I took my time and landed on this idea.
• 2:52
  SPEAKER_03: I was tinkering on a few different things, uh, but this one really grabbed me because it was based on um a lived experience that I had had before.
• 3:00
  SPEAKER_03: I had grown up with pets, but I had a cat named Simba that was diagnosed with lymphosarcoma and treatment cost$12,000.
• 3:07
  SPEAKER_03: And it was just like flabbergasting to me that I should have been aware ahead of time to have the money to pay for that which I didn't.
• 3:15
  SPEAKER_03: Um, and through learning from that experience, I learned about pet insurance.
• 3:20
  SPEAKER_03: So I started going deep on that.
• 3:22
  SPEAKER_03: Um, and I will say, I mean, I I I imagine some of your listeners are founders that um are at varying stages in their companies.
• 3:30
  SPEAKER_03: Like it took me a while to get this business going.
• 3:33
  SPEAKER_03: Sure.
• 3:34
  SPEAKER_03: Longer than I thought.
• 3:35
  SPEAKER_03: And I was really grateful having heard from a founder friend that was like a couple stages ahead of me that said, look, give yourself like eight months and just like just do research and do whatever comes to you and whatever feels natural.
• 3:48
  SPEAKER_03: Don't feel like you need to get a product out and that you need to raise money and that you need to do blah, blah, blah.
• 3:53
  SPEAKER_03: And that was really helpful for me to just give myself permission to tinker and to iterate.
• 3:57
  SPEAKER_03: Um and we launched the business.
• 4:00
  SPEAKER_03: And yeah, I have lots of stories to share from that.
• 4:03
  SPEAKER_03: But we did end up selling the business late last year, posted about it earlier this year.
• 4:08
  SPEAKER_03: Um yeah.
• 4:11
  SPEAKER_01: Yeah, I've never met a founder who was able to get it off the ground in a very rapid time and scale it up quickly.
• 4:18
  SPEAKER_01: I mean, you know, you the thing, the reason I started my TV show and this podcast is because, you know, a lot of founders, I I I mentor and uh and coach, but I mentor at the University of Maryland and Johns Hopkins School of Entrepreneurship.
• 4:35
  SPEAKER_01: And a lot of the young entrepreneurs were they just had this weird idea that they were getting from YouTube and social media about how to start businesses, and they were getting these, you know, oh, I started a side gig on a Friday, and by Tuesday I was doing$10 million a year, and now I'm retired.
• 4:53
  SPEAKER_01: It's like it's all garbage.
• 4:54
  SPEAKER_01: And I've never met anybody who was able to do it.
• 4:57
  SPEAKER_01: And my personal experience with building brands is, you know, I mean, uh it's gone anywhere from taking me two, three, four years to get it moving in the right direction to, you know, one to two years, but never simple.
• 5:10
  SPEAKER_01: It never goes according to plan.
• 5:12
  SPEAKER_01: And everybody's got to pivot and everybody's gotta do things differently.
• 5:16
  SPEAKER_01: So um and I've spoken to over at this point, over 2,500 founders, and not not one of them has ever said, I laid out this plan.
• 5:25
  SPEAKER_01: It started in February, and by December, everything went according to plan.
• 5:29
  SPEAKER_01: And by the following year, we were at a hockey stick.
• 5:32
  SPEAKER_01: It's never, it's never happened.
• 5:33
  SPEAKER_03: So Yeah.
• 5:34
  SPEAKER_03: I I couldn't agree more.
• 5:36
  SPEAKER_03: And I think having that expectation, having the expectation going in that it will take time and we have to um like embrace the unknown and it may not go according to the plan that we first devise in our head, I think it's very healthy.
• 5:48
  SPEAKER_03: And I think Yeah, it it took me uh it took me years of working on my company to then like really realize that actually the most important growth is the growth that happens within that precedes the outer results.
• 6:03
  SPEAKER_03: Like when I have looked inward in a very like um very intentional way, that's what has led me to be able to achieve more with actually less grinding, less hustle, less fear, less trying to control.
• 6:18
  SPEAKER_03: Um, and that's made all the difference.
• 6:20
  SPEAKER_03: And to me, that's worth all um more than all the gold in the world is uh understanding more about myself.
• 6:27
  SPEAKER_01: I one I couldn't agree more.
• 6:30
  SPEAKER_01: I I founded my first business when I was 27 years old, and it was an absolute disaster.
• 6:35
  SPEAKER_01: And it was not because the business model was bad, it wasn't because the location was bad, it was a retail.
• 6:40
  SPEAKER_01: Actually, all that worked out well.
• 6:42
  SPEAKER_01: This the business was busy, but the place ran like terribly, and it was j every day was just madness.
• 6:50
  SPEAKER_01: And it was my own fault because I was a terrible leader and I was a terrible manager and I was a terrible process developer, and it was just awful.
• 6:57
  SPEAKER_01: And I did it for four years, and I I worked, you know, seven days a week, 12, 14 hours a day, and I just couldn't get out of the grind, and it was 100% because of me.
• 7:06
  SPEAKER_01: But when I I sold it, I was smart enough to own the real estate, and I've sold it, so I walked away a little bit.
• 7:12
  SPEAKER_01: But it took me a good year and a half of reflection to determine that it was me and the things that I needed to do to work on, so that my second business was successful, my third business was was successful.
• 7:27
  SPEAKER_01: But, you know, along the way, I still do, I still reflect back almost every week on all the things I messed up on the week that I'm in.
• 7:36
  SPEAKER_01: Because I I still make mistakes.
• 7:37
  SPEAKER_01: I still make stupid mistakes and do dumb things.
• 7:40
  SPEAKER_01: But, you know, as long as you don't do them over and over again, you know, you don't do the same mistakes over and over again.
• 7:48
  SPEAKER_01: You just make different ones.
• 7:50
  SPEAKER_03: Exactly.
• 7:51
  SPEAKER_03: Like I hear a lot, you know, trial and error.
• 7:53
  SPEAKER_03: And yeah, that's true.
• 7:54
  SPEAKER_03: We make mistakes, but really it's like trial and learning, right?
• 7:57
  SPEAKER_03: You try something, you yeah, like maybe it didn't go the way that you would have preferred.
• 8:02
  SPEAKER_03: That happens a lot.
• 8:03
  SPEAKER_03: And when that does, like looking at what what what was it about that and what could I have done better?
• 8:08
  SPEAKER_03: Could I have uh could I have responded better to that?
• 8:12
  SPEAKER_03: Did I need to react instantly to that?
• 8:15
  SPEAKER_03: Could I have uh been a little calmer?
• 8:17
  SPEAKER_03: Um, could I have been more introspective?
• 8:20
  SPEAKER_03: And yeah, I think the whole um the whole reason I have to get deep for a second, but I am, is I I feel like the whole point of life is to evolve and to learn and to go.
• 8:31
  SPEAKER_01: Absolutely.
• 8:32
  SPEAKER_03: So I've always been really interested in this growth of self, growth within self, because I think that that directly relates to the the growth in the like in whatever we're pursuing and the results that we're seeing with our companies.
• 8:45
  SPEAKER_03: Starting a company is a very spiritual, very transformative, deeply transformative journey.
• 8:50
  SPEAKER_03: It ha it was for me.
• 8:52
  SPEAKER_01: I I I couldn't agree more.
• 8:54
  SPEAKER_01: I mean, it's I I can look back on my life and I can see all the different steps along the way that started with business and how I did things and where I am today because of it.
• 9:06
  SPEAKER_01: And it still, you know, you were just talking about, you know, could I have reacted different to this and that?
• 9:11
  SPEAKER_01: I didn't realize I I grew up in New York, and I I'm definitely a New Yorker, and I have a very strong and to boot an Italian New Yorker, so I'm I'm very um use my hands a lot, but I also speak very forcefully.
• 9:26
  SPEAKER_01: And I didn't realize I, you know, my wife and I have five children, and I didn't realize until I started working from home how much that affects people around me.
• 9:39
  SPEAKER_01: Because when I'm on a call like this and and I'm, you know, we're in a discussion about business, and I happen to raise my voice.
• 9:47
  SPEAKER_01: I'm not doing it like people who know me, people who work with me, know that I'm not doing it to like chastise anybody.
• 9:52
  SPEAKER_01: It's just the way I am.
• 9:53
  SPEAKER_01: Like I'll I'll I I get into it, and my kids were like, oh my God, Phil's yelling again.
• 9:59
  SPEAKER_01: And I'm like, am I yelling?
• 10:01
  SPEAKER_01: They're like, oh, he's yelling, he's yelling.
• 10:03
  SPEAKER_01: Mom, he's yelling, you know.
• 10:05
  SPEAKER_01: And my wife is like, Why are you yelling?
• 10:06
  SPEAKER_01: I'm like, I'm not yelling.
• 10:08
  SPEAKER_01: But it's just the way I say things.
• 10:10
  SPEAKER_03: It's so relatable.
• 10:11
  SPEAKER_03: I was just talking to one of my close friends this morning about this, where like the people around us feel us the most.
• 10:18
  SPEAKER_03: Like my co-founder, uh, like re like he's we spent a lot of time together for six years building and then selling business.
• 10:26
  SPEAKER_03: It's like a man.
• 10:28
  SPEAKER_03: A hundred percent.
• 10:29
  SPEAKER_03: And so he would, I had my emotional roller coaster, truly, at that time, a little less so, you know, more consistent now.
• 10:37
  SPEAKER_03: Thankfully, I've learned.
• 10:39
  SPEAKER_03: But that's but that's just life.
• 10:40
  SPEAKER_03: And so he feels it, and the ripple effects are truly large.
• 10:43
  SPEAKER_03: And I also think it speaks to something that I've learned too, is when I first started my journey, I really wanted to help millions of people.
• 10:53
  SPEAKER_03: I just like I had this burning desire to help as many people as possible.
• 10:57
  SPEAKER_03: Like having a finite cap on the number of people that I could impact, like really just like it hurt my soul.
• 11:03
  SPEAKER_03: I was like, no.
• 11:05
  SPEAKER_03: And I think that that, yeah, like it just I was hungry.
• 11:08
  SPEAKER_03: I wanted to help as many people as possible.
• 11:10
  SPEAKER_03: And I'm realizing now that helping just one person may also be enough.
• 11:15
  SPEAKER_03: Helping one person, because it changing one person's life, like truly changing it, like changing their actual life, like having a profound impact on their life.
• 11:25
  SPEAKER_03: And then they have the ripple effect.
• 11:27
  SPEAKER_03: So they're going out, every single person that they're talking to, their family members, their loved ones, their relationships, their coworkers, every single person that they interact with day to day now and for the foreseeable future, like that is actually profound impact that I didn't clock when I was at the beginning of my journey.
• 11:43
  SPEAKER_03: And even as a little kid, I was like, oh, I don't want to do these professions that my impact will be finite.
• 11:48
  SPEAKER_03: Like I want to just I want it to be able to scale, like always scale.
• 11:52
  SPEAKER_03: But I think the tough thing also about founders in the early days is like growth, you have to do things that don't scale.
• 11:58
  SPEAKER_03: Like I did, I posted on my dog's Instagram to then get our first customers that didn't know me personally, and they were like dog moms in New York City.
• 12:06
  SPEAKER_03: Um, and because they followed the account, and I posted so much content and it was a full-time job, social media, and like I've probably undervalued, I definitely undervalued my.
• 12:15
  SPEAKER_03: I think founders do this.
• 12:16
  SPEAKER_03: We undervalue our time in the very beginning days because we're like, oh, why don't we just test things, blah, blah, blah.
• 12:21
  SPEAKER_03: So I could have hired someone sooner.
• 12:23
  SPEAKER_03: Um, but we genuinely do have to do things that don't scale at the beginning.
• 12:26
  SPEAKER_01: Well, I I think in the beginning you're trying to figure out, at least, you know, for us, we've always, you know, and I've done four successful ones, and and you're always trying in the beginning to figure out your product market fit and who your customer is and really hone in on it.
• 12:45
  SPEAKER_01: So you're trying to do everything even if you have people, you're trying to do everything or be involved in everything because you have to be.
• 12:54
  SPEAKER_01: You're trying to figure it out and so that you can build the systems that scale.
• 13:00
  SPEAKER_01: So in the beginning you have to.
• 13:01
  SPEAKER_01: You have to stay close and then once you have it figured out, then you can put together the systems and the processes to scale.
• 13:10
  SPEAKER_01: But in the beginning, I think every founder needs to stay very, very close to um you know, social media, wherever you're talking to the customer.
• 13:20
  SPEAKER_00: I agree.
• 13:22
  SPEAKER_01: Yeah, I'll tell you, we uh I I I did this uh I I I did this uh uh a startup of retail stores in in DC and we got acquired by a supermarket chain and it was great and we had fun doing it, and then we moved into uh a beauty products line we built with a woman named Carol, she was a model and we were the far first raw um beauty line based on the principles of raw lifestyle.
• 13:52
  SPEAKER_01: And then from there, I built this um shaving brand and we had a deal with uh Chick with Energizer.
• 14:00
  SPEAKER_01: We were the first people they ever private labeled a razor for and uh for men and women.
• 14:06
  SPEAKER_01: And but we were more focused on like the total shave, not just selling cheap razors, but selling a great shave.
• 14:11
  SPEAKER_01: We had skincare and it was beautiful.
• 14:14
  SPEAKER_01: But it didn't go anywhere the first couple of months, and you know, we were sitting there looking at each other, going, we've done this twice already, and everything worked, right?
• 14:23
  SPEAKER_01: And we followed these steps and we learned along the way, so we made changes and now we're doing this.
• 14:28
  SPEAKER_01: Nothing worked.
• 14:29
  SPEAKER_01: We we tried advertising, it didn't work.
• 14:31
  SPEAKER_01: Messaging, website, we we we just couldn't it wasn't breaking through.
• 14:36
  SPEAKER_01: And we were frustrated.
• 14:38
  SPEAKER_01: It was like two years.
• 14:39
  SPEAKER_01: I mean, we were doing sales, but nothing nothing like what we projected to do, nothing like what we needed to do.
• 14:45
  SPEAKER_01: And uh and I woke up one morning and I was reading the sports news and I saw that there was this guy, Brian Wilson, who was a pitcher for the San Francisco Giants, and he had this b big beard.
• 14:57
  SPEAKER_01: And Major League Baseball hated him because of it.
• 14:59
  SPEAKER_01: They wanted him to be clean-shaven, he wouldn't shave, but but nobody would do anything about it because he was a great great pitcher.
• 15:06
  SPEAKER_01: But he had uh injured his elbow, he had Tommy John surgery, they they traded him to the Dodgers.
• 15:11
  SPEAKER_01: It's the first time he was going to pitch in a year.
• 15:14
  SPEAKER_01: So I sent a message to his people.
• 15:16
  SPEAKER_01: This is I'm having coffee, it's six o'clock in the morning.
• 15:19
  SPEAKER_01: I sent a message to his people.
• 15:21
  SPEAKER_01: I said, I will pay Brian one million dollars to shave with our razor and shave cream and you know, and so they responded back a couple hours later with an email and said, we will run this past Brian.
• 15:37
  SPEAKER_01: And that's all I needed because now I could legitimately, without lying, say, I am in discussion to pay Brian Wilson a million dollars to shave with our razor.
• 15:44
  SPEAKER_01: So I gave it to the PR firm and it just went everywhere.
• 15:48
  SPEAKER_01: And people were pissed at us.
• 15:51
  SPEAKER_01: They were we only had at the time, we only had Facebook, a little bit of Instagram, um, and then uh yeah, Twitter.
• 15:59
  SPEAKER_01: But that was about it.
• 16:01
  SPEAKER_01: And um they were the people were just screaming at us and then sending us pictures of every single body part, some not shaped safe for work, uh with a price tag on it.
• 16:11
  SPEAKER_01: I'll shave this for 10 grand, I'll shave this for five grand, I'll shave this, and it just exploded.
• 16:15
  SPEAKER_01: Then all the sports uh channels were calling us up, interviewing us to f figure out what kind of mad guy is is willing to pay a million bucks to get some guy to shape with his shape cream.
• 16:27
  SPEAKER_01: And uh Yeah, and we it we were in the news everywhere.
• 16:32
  SPEAKER_01: Japan, France, I mean everybody was it went absolutely nuts.
• 16:35
  SPEAKER_01: And that really launched us and got us orders, right?
• 16:39
  SPEAKER_01: And and this went on for about you know about two weeks, as these things do, and then it started to die off.
• 16:46
  SPEAKER_01: And then TMZ catches Brian coming out of a gym in sa in LA and they asked him, Are you gonna take the million bucks to shave your beard?
• 16:53
  SPEAKER_01: And he he goes on this expletive rant about he's not shaving for any effing money and blah, blah, blah.
• 16:59
  SPEAKER_01: And he goes nuts again.
• 17:01
  SPEAKER_01: Everybody's pissed off that a guy would turn down a million bucks, right?
• 17:05
  SPEAKER_01: So anyway, it lasted about a month.
• 17:06
  SPEAKER_01: But that really took that to launch us.
• 17:09
  SPEAKER_00: Amazing publicity.
• 17:10
  SPEAKER_01: And that was like the only thing that that really helped us.
• 17:15
  SPEAKER_01: Um but that's amazing.
• 17:16
  SPEAKER_03: That on a whim, you see this and you just do your shot.
• 17:20
  SPEAKER_03: You're like, you know what?
• 17:21
  SPEAKER_03: I mean, yeah, a million dollars, I didn't expect you to be able to offer that much.
• 17:25
  SPEAKER_03: So that's really cool.
• 17:26
  SPEAKER_03: But even if it was less, you just off the cuff, you had this thought.
• 17:30
  SPEAKER_03: I feel like the more early morning intuitive hits, like that really hit for me too, more with fundraising than with growth.
• 17:36
  SPEAKER_03: Um, but I had been having a hard time raising a particular round.
• 17:41
  SPEAKER_03: And I just finally was like, you know what?
• 17:43
  SPEAKER_03: And I just woke up early one morning and I thought, what if, what if this investor that I know wakes up early is awake right now?
• 17:49
  SPEAKER_03: I'm like, what are the odds?
• 17:50
  SPEAKER_03: Why don't I just give him a call?
• 17:51
  SPEAKER_03: Gave him a call, he invested.
• 17:53
  SPEAKER_03: Galvanized by that.
• 17:54
  SPEAKER_03: I was like, what about my other investor that's also an early morning riser?
• 17:57
  SPEAKER_03: Why don't I call her?
• 17:58
  SPEAKER_03: She also invested.
• 17:59
  SPEAKER_03: And before like 8 30 in the morning, I'd raised all the money that I needed to raise, and it was one morning.
• 18:03
  SPEAKER_01: Yeah.
• 18:04
  SPEAKER_01: Yeah.
• 18:05
  SPEAKER_01: Sometimes it just hits.
• 18:06
  SPEAKER_01: Raising money, and I tell all the people I coach, all the founders, you know, everybody wants to raise money.
• 18:13
  SPEAKER_01: And I say, raising money is one of the hardest things you're ever going to do because you have to be very strategic about it.
• 18:19
  SPEAKER_01: You have to know what you're doing, you have to know what you're going after.
• 18:22
  SPEAKER_01: And you can't go into a meeting acting like you're looking for a handout.
• 18:26
  SPEAKER_01: You have to go in there that you're confident enough to say, I'm presenting you with an opportunity, you know.
• 18:31
  SPEAKER_03: Yeah, you're the lucky one.
• 18:33
  SPEAKER_01: Yeah, people don't people go in there, it's like, you know, they think it's a numbers game.
• 18:37
  SPEAKER_01: It to a certain extent, it is a numbers game, but you have to be strategic.
• 18:41
  SPEAKER_01: You can't just take your your pitch deck and blast it out to 10,000 PE guys.
• 18:46
  SPEAKER_01: I would say that 9,999 of them are not going to read it.
• 18:50
  SPEAKER_01: That it's just a it's annoying.
• 18:52
  SPEAKER_01: You know, because you you and a thousand others are also doing the same thing.
• 18:56
  SPEAKER_01: So it's uh it's one of the hardest things to do in business is to raise capital.
• 19:01
  SPEAKER_01: So sometimes, you know, getting out there first thing in the morning while they're just getting to their desk or even before, if you can get them on the phone and go through it.
• 19:09
  SPEAKER_03: Like he had just landed off of a flight and was pleasantly surprised to hear.
• 19:13
  SPEAKER_03: And it was just a phone call.
• 19:14
  SPEAKER_03: I was laying on this giant yoga mat in my place.
• 19:18
  SPEAKER_03: And I was just this, and I just I hopped at the call.
• 19:20
  SPEAKER_03: It was a quick, it was a short call, too.
• 19:23
  SPEAKER_03: And I just I feel like the ones that are more authentic uh have always been the most efficient, like the highest ROI of my time, as opposed to, okay, I'm gonna go out there and expect to get a hundred no's and I'm gonna find my uh yeah, I I do feel like so much of it is energy and like alignment.
• 19:42
  SPEAKER_03: Um, and there's luck for sure.
• 19:44
  SPEAKER_01: Yeah.
• 19:45
  SPEAKER_01: Oh, yeah, there's definitely luck involved.
• 19:47
  SPEAKER_01: But as long as you, you know, if you have a a business with and you can tell the story correctly and you're confident enough, because they're investing in the entrepreneur just as much as they're investing.
• 19:56
  SPEAKER_01: You know, one one uh PE guy that I know told me, he said it time and time again, he said, we'd rather invest in an A player with a B product than a B player with an A product, because we know that the A player can turn that B product into a success and improve it.
• 20:11
  SPEAKER_01: A B player can take an A product and turn it into a B product very quickly.
• 20:16
  SPEAKER_01: And so they're always looking at the investor.
• 20:18
  SPEAKER_01: I mean, at the uh at the entrepreneur just as much.
• 20:21
  SPEAKER_01: I'll tell you a funny I'll tell you a funny cold calling uh investor story.
• 20:26
  SPEAKER_01: This was early on.
• 20:28
  SPEAKER_01: I had um we had these stores and we had put our money in and we had built three stores on our own.
• 20:34
  SPEAKER_01: And now we wanted to do an acquisition and we needed more money, and we wanted to raise eleven million dollars to to build more stores in downtown DC.
• 20:42
  SPEAKER_01: And so we were hitting the we were hitting investors hard.
• 20:46
  SPEAKER_01: And and we just couldn't we couldn't get anywhere.
• 20:49
  SPEAKER_01: And we were like pissed off, and I said, you know, I'm just gonna start being a little bold.
• 20:54
  SPEAKER_01: So I started, you know, contacting anybody I could.
• 20:56
  SPEAKER_01: I love it.
• 20:57
  SPEAKER_01: And there was, you know, who Jerome Kohlberg, Kohlberg, Travis and Roberts, but Jerome Kohlberg, he was one of the founders, but he had left KKR and started his own thing, Kohlberg and company.
• 21:09
  SPEAKER_01: And uh the only phone number I could get was his home phone number.
• 21:13
  SPEAKER_01: It's the only number I could get.
• 21:15
  SPEAKER_01: I couldn't get his office, I couldn't get his email, I couldn't get anything.
• 21:18
  SPEAKER_01: All I could get was his home phone number.
• 21:20
  SPEAKER_01: So I called it.
• 21:21
  SPEAKER_01: And I said, It's Mr.
• 21:22
  SPEAKER_01: Kohlberg there.
• 21:23
  SPEAKER_01: Yeah.
• 21:23
  SPEAKER_01: They get him on the phone.
• 21:24
  SPEAKER_01: And I said, you know, this is Phil Massiello, and I start going through my my spiel.
• 21:28
  SPEAKER_01: And he's like, Who, who is this?
• 21:30
  SPEAKER_01: I said, it's Phil Massiello.
• 21:32
  SPEAKER_01: I found it, blah, blah, blah, blah, blah.
• 21:33
  SPEAKER_01: And I'm trying, you know, we have stores in DC.
• 21:36
  SPEAKER_01: I said, and this is what we do.
• 21:37
  SPEAKER_01: He's like, Well, how'd you get my number?
• 21:40
  SPEAKER_01: I said, I I I don't know.
• 21:41
  SPEAKER_01: I said, uh, somebody gave it to me.
• 21:43
  SPEAKER_01: I said, but you know, he's like, so you're calling me at home.
• 21:46
  SPEAKER_01: I said, well, I couldn't get your office.
• 21:48
  SPEAKER_01: I said, I couldn't get your office number.
• 21:50
  SPEAKER_01: I said, and you know, I wanted to talk to you.
• 21:52
  SPEAKER_01: I think it would be something you'd be interested in.
• 21:54
  SPEAKER_01: And then he goes, There's like silence.
• 21:55
  SPEAKER_01: He goes, All right, tell me about the business.
• 21:57
  SPEAKER_01: So I tell him about the business.
• 21:58
  SPEAKER_01: And then uh we we go on.
• 22:00
  SPEAKER_01: For about 15 minutes.
• 22:01
  SPEAKER_01: And then he goes, So you decided to call me at home.
• 22:05
  SPEAKER_01: I said, I I'm sorry about that, but it's the only number I could get.
• 22:09
  SPEAKER_01: I said, you know, so he's like, you're calling me at home, at home, in my time, in my house.
• 22:14
  SPEAKER_01: I'm like, sorry, but you know, and he's and I'm thinking he's pissed, right?
• 22:17
  SPEAKER_01: And he is a little pissed.
• 22:18
  SPEAKER_01: And then he's like, okay, well, tell me about the business a little bit more.
• 22:21
  SPEAKER_01: Tell me this.
• 22:22
  SPEAKER_01: So I explained it to him.
• 22:24
  SPEAKER_01: We're on the phone for almost an hour.
• 22:26
  SPEAKER_01: And then the last five minutes, he's he's chastising me for calling him at home.
• 22:30
  SPEAKER_02: And how bold.
• 22:33
  SPEAKER_02: You're so savage.
• 22:34
  SPEAKER_02: But then he's on the phone for an hour.
• 22:35
  SPEAKER_02: He's interested in the phone.
• 22:37
  SPEAKER_01: What could he do?
• 22:37
  SPEAKER_01: Beat me up?
• 22:38
  SPEAKER_01: So he hangs up the phone, and I'm thinking, well, if nothing else, it's a good learning experience because, you know, it built me thicker skin because now I just got chastised for calling the guy, but at least he heard the pitch.
• 22:51
  SPEAKER_01: Two days later, we get a phone call.
• 22:54
  SPEAKER_01: Mr.
• 22:54
  SPEAKER_01: Colbert would like to see you in his office tomorrow morning at 10 a.m.
• 22:59
  SPEAKER_01: No problem.
• 22:59
  SPEAKER_01: This is like two in the afternoon.
• 23:01
  SPEAKER_01: We're in DC, he's in New York.
• 23:03
  SPEAKER_01: So, you know, I immediately drop, go grab stuff at home, drive up to New York, you know, get a hotel room close to his office, and go in there the next morning.
• 23:14
  SPEAKER_01: And I'm thinking the worst.
• 23:15
  SPEAKER_01: I'm thinking he's gonna yell at me.
• 23:18
  SPEAKER_01: So we get there and um had a presentation all ready and uh walk in and and you know, they send me into this conference room, and there's a couple other people in there.
• 23:29
  SPEAKER_01: And I'm sort of, you know, a little nervous because I'm thinking this guy's gonna come in and chastise me.
• 23:34
  SPEAKER_01: He walks in, he's he's he he was very uh he had a very distinct look.
• 23:39
  SPEAKER_01: He was bald and he's in this this like tweed jacket that looks like he looks like he just crumbled it up out of the backseat of his car, right?
• 23:47
  SPEAKER_01: He comes in and he looks at it, he goes, he goes, This is the guy that cold called me at home.
• 23:54
  SPEAKER_01: Cold called me at home.
• 23:55
  SPEAKER_01: And I'm thinking, here it comes.
• 23:57
  SPEAKER_01: He goes, now I want you to explain the business to all these people.
• 24:01
  SPEAKER_01: I'm like, okay, so I I start going, you know, and I'm explaining the peep the business.
• 24:06
  SPEAKER_01: And he goes, and so then I'm I'm done.
• 24:08
  SPEAKER_01: He goes, you know why I called you in?
• 24:10
  SPEAKER_01: I said, to yell at me for cold calling you at home and embarrass me in front of all these people.
• 24:16
  SPEAKER_01: No, that's not why.
• 24:17
  SPEAKER_01: He said, I called you in because uh after I got off the phone with you, I was thinking, we're invested heavily in this business and it's not going so well in this one business.
• 24:24
  SPEAKER_01: But what you were talking about, it sounds like it could be a fit to this other business and we could blend them together and we might have something.
• 24:31
  SPEAKER_01: He said, because frankly,$11 million, I don't invest$11 million.
• 24:36
  SPEAKER_01: He said, the legal fees will kill you.
• 24:38
  SPEAKER_01: He said, we don't do anything for less than 20.
• 24:40
  SPEAKER_01: He said, just because of the legal fees, but there might be an opportunity.
• 24:43
  SPEAKER_01: He said, so I'm gonna come down to Washington, D.C.
• 24:46
  SPEAKER_01: next week.
• 24:46
  SPEAKER_01: You're gonna take me around to your stores, you're gonna explain the business, and I'm gonna explain this business to you.
• 24:51
  SPEAKER_01: I was like, okay, and I left.
• 24:54
  SPEAKER_01: And he came down the following week.
• 24:56
  SPEAKER_01: Couldn't have been nicer.
• 24:57
  SPEAKER_01: He was a great guy.
• 24:57
  SPEAKER_01: We spent an entire day going through the business.
• 25:00
  SPEAKER_01: And then he was explaining what he wanted to do.
• 25:02
  SPEAKER_01: We worked on it for about a month.
• 25:04
  SPEAKER_01: We couldn't, it just never materialized.
• 25:06
  SPEAKER_01: But I wound up having a relationship with the guy for years.
• 25:10
  SPEAKER_01: He was just a he was just a smart, great guy.
• 25:13
  SPEAKER_01: And he said to me one day, like a couple of months afterwards, he goes, you know, he goes, I was really pissed that you called me at home.
• 25:20
  SPEAKER_01: And then I thought to myself, that's a guy that wants to get something done.
• 25:26
  SPEAKER_01: He goes, So as much as I was pissed, he said, I sort of respected it, but I wouldn't do it again.
• 25:32
  SPEAKER_01: I said, I'll never do it to you again.
• 25:35
  SPEAKER_03: I love that.
• 25:36
  SPEAKER_03: Truly, I am such a big proponent of the shoot your shot mentality.
• 25:41
  SPEAKER_03: You gotta do it.
• 25:42
  SPEAKER_03: Like, if not now, when?
• 25:43
  SPEAKER_03: And if not you, then who?
• 25:45
  SPEAKER_03: Like to send it.
• 25:46
  SPEAKER_03: Exactly.
• 25:46
  SPEAKER_03: If you have the idea, try it.
• 25:48
  SPEAKER_03: What's the worst that could happen?
• 25:49
  SPEAKER_03: Yeah, maybe a little chastising, maybe a little, maybe a little embarrassing in front of other people.
• 25:54
  SPEAKER_03: But like who actually cares?
• 25:56
  SPEAKER_03: And the story alone is like, is amazing, much less like any the fact that it kept going and that you guys were able to even see if it could come to fruition, you know?
• 26:06
  SPEAKER_03: And I feel like those are things that you just you can't plan and you can't over-engineer.
• 26:10
  SPEAKER_03: Like it is listening to your gut.
• 26:12
  SPEAKER_03: You're like, yeah, oh, that's tough on the home phone number.
• 26:15
  SPEAKER_03: I can't get anything else, and really try, can't get anything else.
• 26:18
  SPEAKER_03: But you're like, I'm just, I'm just gonna try it.
• 26:20
  SPEAKER_03: And I think we've had similar stories with our growth with for sure, where like we were trying and trying to grow it.
• 26:25
  SPEAKER_03: And I was like, I really don't want to spend all this money on Facebook ads.
• 26:28
  SPEAKER_03: Like I worked at Facebook on ads, and I was like, Do I really want to take the money that I just worked so hard to fundraise for and just channel into ads?
• 26:34
  SPEAKER_03: Like, no one wants that.
• 26:35
  SPEAKER_03: Um, and I get this inbound email from a man who runs a YouTube channel called Boston Terrier Society.
• 26:44
  SPEAKER_03: And he's like, Would you like to come on and talk about pet insurance?
• 26:47
  SPEAKER_03: Our audience would like to know.
• 26:48
  SPEAKER_03: And it looked like small but cute.
• 26:51
  SPEAKER_03: And I just I had a good feeling about it.
• 26:53
  SPEAKER_03: I was like, you know what, Donnie?
• 26:54
  SPEAKER_03: Yes, I will.
• 26:55
  SPEAKER_03: So I come on and we chat.
• 26:57
  SPEAKER_03: And I'm kind of it's my first time getting posted on YouTube.
• 27:00
  SPEAKER_03: And so I just I did my best.
• 27:03
  SPEAKER_03: Um, and we posted it.
• 27:04
  SPEAKER_03: And coincidentally, he had been researching all the topics that dog owners, specifically Boston Terror um owners, had been asking.
• 27:14
  SPEAKER_03: And so he knew exactly how to play it with SBO, with YouTube, all that, and it blows up.
• 27:19
  SPEAKER_03: And so this was the single largest um inbound segment of leads that we consistently got over time was because I was a guest for like, I don't know, 10 minutes on the Boston Terror Society on the YouTube channel.
• 27:33
  SPEAKER_03: And it's just a big proponent.
• 27:35
  SPEAKER_01: I am a huge proponent of PR.
• 27:37
  SPEAKER_01: I tell people all the time, you know, founders always want to start running ads.
• 27:40
  SPEAKER_01: And I say, ads are a support mechanism.
• 27:42
  SPEAKER_01: Your messaging has to get out there in a different way.
• 27:44
  SPEAKER_01: So that's great.
• 27:47
  SPEAKER_03: I also um we experimented a little bit with TikTok and hearing about your thing that went viral.
• 27:52
  SPEAKER_03: We had one video that went viral, and it was just me walking in New York City because I lived there for a time.
• 27:57
  SPEAKER_03: So did my co-founder, and I just took a video of me.
• 27:59
  SPEAKER_03: I was walking my dog, and I was like, Did you know that most pet insurance makes you pay up front and out of pocket, kind of just like a little nugget?
• 28:05
  SPEAKER_03: And I just spoke from the heart off the cuff, and that thing went viral.
• 28:10
  SPEAKER_03: Like many, many, many, many, many people saw it.
• 28:13
  SPEAKER_03: Um, and yeah, it's so interesting that we like we really can't control or plan how things like outcomes don't belong to us.
• 28:21
  SPEAKER_03: As founders, we are, we have to have this like delusional belief that whatever we do, it's gonna be a success.
• 28:27
  SPEAKER_03: And, you know.
• 28:28
  SPEAKER_03: But I also think the some of the best things come from just seemingly nowhere, like out of like out of the unknown.
• 28:35
  SPEAKER_03: And it takes a little bit of action from us, a little bit of courage, like a little bit of bravery, but then it works out better than we ever could have imagined.
• 28:43
  SPEAKER_01: You know, I just had um this woman, Amy McCord, on my show.
• 28:49
  SPEAKER_01: Uh, she um she had um built a um a uh uh flower moxie.
• 28:58
  SPEAKER_01: And it's uh she took essentially the blue apron concept and applied it to flowers.
• 29:04
  SPEAKER_01: So people want to build their own floral arrangements and she gives you basically the product and the recipes and a video.
• 29:11
  SPEAKER_01: And I mean she's exploded, she's done well.
• 29:14
  SPEAKER_01: And she said two things.
• 29:15
  SPEAKER_01: She said, you know, people always say follow your passion when you build a business.
• 29:20
  SPEAKER_01: She said, and I don't believe in that because if you follow your passion and your business becomes based on your passion, then you hate your passion after a while because business is business.
• 29:28
  SPEAKER_01: She said, But at if at three o'clock in the morning you're still up and you're um you know, you're Googling like uh Victorian wedding dresses, then that's something that you can build a business around because that's something that you're interested in.
• 29:44
  SPEAKER_01: It's not your passion, but you've got this interest and you want to learn about it.
• 29:47
  SPEAKER_01: She said, and that you can build a business about.
• 29:50
  SPEAKER_01: But the other thing she said, which I think is more profound, is she said don't wait for permission to do something.
• 29:57
  SPEAKER_01: Put yourself out there.
• 29:58
  SPEAKER_01: What's the worst that could happen?
• 29:59
  SPEAKER_01: She said, I I am she's she said that she's a um a uh uh a something introvert.
• 30:07
  SPEAKER_01: She's an introvert, but she's she's okay with like talking to people.
• 30:11
  SPEAKER_01: But you know, she's hesitant.
• 30:12
  SPEAKER_01: But she said, you know, um they came to me, my a publisher came to me and asked me to write a book about floral arranging.
• 30:19
  SPEAKER_01: And I didn't want to I put it off for a year.
• 30:21
  SPEAKER_01: I didn't want to do it because I thought to myself, I'm gonna put myself out there and people are gonna criticize the book and they're gonna criticize me and you know people on social.
• 30:28
  SPEAKER_01: And then I thought to myself, who gives it who cares?
• 30:31
  SPEAKER_01: She said, I'm just gonna do it.
• 30:33
  SPEAKER_01: And she did it, and the book is a success, and it's a great book.
• 30:36
  SPEAKER_01: But I said, you know, I I went through the same thing.
• 30:38
  SPEAKER_01: I said, I I wrote four four books.
• 30:40
  SPEAKER_01: You know, people criticize some of them.
• 30:42
  SPEAKER_01: I don't really care if they did or not, because all I respond to them is, send me your book.
• 30:47
  SPEAKER_01: Well, you don't have one?
• 30:48
  SPEAKER_01: Oh, okay.
• 30:50
  SPEAKER_01: Sorry.
• 30:50
  SPEAKER_01: And that's exactly how I respond to people on social media when they say something.
• 30:54
  SPEAKER_01: I go, oh, send me your book.
• 30:55
  SPEAKER_01: Oh, oh, sorry, you don't have one.
• 30:57
  SPEAKER_01: I just looked it up.
• 30:58
  SPEAKER_01: So, you know, when you write one, let me know and I'll criticize your book.
• 31:03
  SPEAKER_01: So, you know, I I don't because people on social media, they they do stuff, you know, everybody thinks they have a voice.
• 31:10
  SPEAKER_01: So anyway.
• 31:12
  SPEAKER_03: I loved what you said about the the passion um and not turning that into a business, because I can super like there's there's something that I just really love doing.
• 31:21
  SPEAKER_03: And I have that feeling that if I turn it into a business, then I will burn out on it and not enjoy it.
• 31:25
  SPEAKER_03: And so I will not be doing that.
• 31:26
  SPEAKER_03: But the thing that I research late at night on my own, like that, the thing that I'm ever deeply rabbit hole fascinated by, like that is the thing.
• 31:36
  SPEAKER_03: Um, and I also love what you said about don't wait for permission.
• 31:39
  SPEAKER_03: And I do think we need to have thick skin.
• 31:41
  SPEAKER_03: Like there are a lot of people who would like to criticize, you know?
• 31:44
  SPEAKER_03: Um, and I think other people and like maybe they don't feel seen in their own lives, and so they need to take to the to the internet.
• 31:53
  SPEAKER_03: And yeah, I really do believe hurt people hurt other people.
• 31:56
  SPEAKER_03: And so that that's the reality.
• 31:58
  SPEAKER_03: And I also like this idea that like it's not gonna be for everyone because it's coming from an authentic place.
• 32:04
  SPEAKER_03: Like I think I've spent a lot of my a lot of my like career like trying to be impressive, like because I like young me wanted to impress my mom.
• 32:12
  SPEAKER_03: And so I spent a lot of time like getting all these achievements to then, you know.
• 32:16
  SPEAKER_03: Um, but that but that it wasn't coming from an authentic place.
• 32:20
  SPEAKER_03: And that was more like, oh, I want everyone to be happy with my message and what I'm putting out there and to be perceived in a pleasant way, but that comes at a cost, right?
• 32:30
  SPEAKER_03: It comes at a cost of actually saying what we want to say and doing the thing that we want to do and living a life that's true to us and not what other people expect of us.
• 32:37
  SPEAKER_03: So I feel really passionately about that.
• 32:39
  SPEAKER_03: And I know that it's gonna come at um at uh at another cost of like not everyone's gonna like it.
• 32:46
  SPEAKER_03: Like the right people are gonna listen to the message that we have to say and really align with it and and take what uh resonates and leave the rest.
• 32:54
  SPEAKER_03: And then the people who don't resonate with it can live their life not listening more to my content.
• 33:02
  SPEAKER_01: I I 100% agree.
• 33:04
  SPEAKER_01: I make content every day, you know, about coaching and about business and about scaling.
• 33:08
  SPEAKER_01: And it's amazing to me some of the message, some of the comments that people make.
• 33:12
  SPEAKER_01: And I just sit there going, dude, all you do is post images of all the bottles of Jack Daniels that you drank, and you're criticizing me.
• 33:25
  SPEAKER_01: I mean, seriously.
• 33:28
  SPEAKER_01: And I leave them up.
• 33:29
  SPEAKER_01: I leave the negative comments up with my comments back because and then people laugh because it's true.
• 33:33
  SPEAKER_01: Like you look at the guy's you look at the guy's profile and he's he's got pictures of like himself drinking Jack Daniels.
• 33:39
  SPEAKER_01: You're going, okay, yeah, you're an achiever.
• 33:43
  SPEAKER_00: I feel like there's they like we have to like love and accept these people from afar.
• 33:52
  SPEAKER_00: Yeah.
• 33:52
  SPEAKER_03: You know?
• 33:54
  SPEAKER_03: Like they have their gifts.
• 33:55
  SPEAKER_03: We don't know what they are, but they have their gifts, and they're they're not showing them right now in this moment.
• 34:02
  SPEAKER_03: Uh, but I'm not going to like be mean to them.
• 34:07
  SPEAKER_01: I am.
• 34:08
  SPEAKER_01: You're gonna be mean to me, I'm gonna be mean to you.
• 34:10
  SPEAKER_01: I I but I do it in a funny way.
• 34:12
  SPEAKER_01: I just throw their own words back at them in a different way.
• 34:15
  SPEAKER_01: But I I cannot, I'm not gonna sit there and say, you know, oh, you know, you know, I understand you.
• 34:21
  SPEAKER_01: I'm not gonna do that.
• 34:22
  SPEAKER_01: It's not my it's not me.
• 34:23
  SPEAKER_01: I'm a I'm I'm a Bronx boy.
• 34:24
  SPEAKER_01: If you were in front of me, I'd throw you out.
• 34:27
  SPEAKER_01: You're a fighter.
• 34:27
  SPEAKER_01: You're a fighter.
• 34:28
  SPEAKER_01: You you're a lover and you're a fighter.
• 34:31
  SPEAKER_01: It's not gonna happen.
• 34:32
  SPEAKER_01: I try.
• 34:33
  SPEAKER_01: I try and be really nice and understanding, but you know, not if you're gonna sit there and be catty on social media.
• 34:39
  SPEAKER_01: Because, you know, those people have no they they think that because they're hidden behind a keyboard, they can say whatever they want.
• 34:45
  SPEAKER_01: And so I like to give it back.
• 34:47
  SPEAKER_01: This way other people look at it and and think twice about leaving stupid comments, number one, and number two, you know, the other people get a kick out of the way I respond because that's just how I am.
• 34:57
  SPEAKER_01: I'm I'm straightforward.
• 34:59
  SPEAKER_03: Yeah, be your humorous self.
• 35:01
  SPEAKER_01: Yeah.
• 35:03
  SPEAKER_01: Yeah, I'm not I can't be that whole uh, you know, oh I can't.
• 35:07
  SPEAKER_03: You can't be Mother Teresa.
• 35:08
  SPEAKER_03: Yeah, yeah.
• 35:09
  SPEAKER_01: I understand hatred with love.
• 35:11
  SPEAKER_01: If you were in front of me, you'd go out the window.
• 35:13
  SPEAKER_01: Um All right.
• 35:15
  SPEAKER_01: Uh we're out of time, but it's been great chit-chatting with you.
• 35:19
  SPEAKER_01: I like uh some of the comments, and uh I maybe we'll talk again.
• 35:24
  SPEAKER_03: Sounds great.
• 35:25
  SPEAKER_03: Thanks so much for having me, Phil.
• 35:26
  SPEAKER_03: I enjoyed it too.
• 35:27
  SPEAKER_01: Yeah, my pleasure.
• 35:28
  SPEAKER_01: How can people get in touch with you if they want to?
• 35:30
  SPEAKER_03: On LinkedIn.
• 35:32
  SPEAKER_01: Just LinkedIn?
• 35:33
  SPEAKER_01: What's your LinkedIn?
• 35:34
  SPEAKER_03: LinkedIn is my LinkedIn is Katherine Denig, my name, D-E-N-N-I-G.
• 35:39
  SPEAKER_03: And then uh they can also follow me on Instagram, which is Katherine.denig.
• 35:43
  SPEAKER_01: Okay, great.
• 35:44
  SPEAKER_01: Fantastic.
• 35:45
  SPEAKER_01: All right, well, hopefully we'll talk again.
• 35:47
  SPEAKER_01: And uh until next time, thank you.
• 35:49
  SPEAKER_00: Thank you.