You Winning Life

Ep. 56-Alyssa Rapp: Leadership and Life Hacks: Insights from a Mom, Wife, Entrepreneur & Executive

August 13, 2020 Jason Wasser, LMFT Season 1 Episode 56
You Winning Life
Ep. 56-Alyssa Rapp: Leadership and Life Hacks: Insights from a Mom, Wife, Entrepreneur & Executive
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You Winning Life
Ep. 56-Alyssa Rapp: Leadership and Life Hacks: Insights from a Mom, Wife, Entrepreneur & Executive
Aug 13, 2020 Season 1 Episode 56
Jason Wasser, LMFT

Life long entrepreneurship is an approach I've been learning more about the last few years.
This week's guest, Alyssa Rapp, is the perfect example of this.
Throughout her career, Alyssa Rapp has not been afraid to ask, Now what?

From training as a competitive gymnast to advising startups and running companies, Alyssa has always been used to working her tail off and looking ahead. By the time she added parenthood to the list, she quickly discovered the need to “hack” the system – find ways to work more efficiently, productively, and achieving at least episodic balance.

Alyssa fell in love with her first entrepreneurial idea while studying at Stanford Business School, and, for the better part of the next decade, ran an e-commerce business called Bottlenotes. Partway through the journey, Bottlenotes pivoted, transforming into a leading digital media company in the US wine industry. From 2015-2017. Alyssa advised startups and private equity-backed companies alike through AJR Ventures; she also taught a course at Stanford’s Graduate School of Business on the Global Dynamics of the Wine Industry.

In 2017, Alyssa and her family decided to move to Chicago where, as of of January 2018, Alyssa was named the CEO of Surgical Solutions by private equity firm Sterling Partners. Within six months, she was named one of Crain’s Chicago’s “Notable Women in Health Care” and made the list for a second year in a row in 2019. Within the same year the company made the 2019 Top 50 Healthcare Companies and Top 100 Leaders in Healthcare.

She is the author of "Leadership and Life Hacks: Insights from a Mom, Wife, Entrepreneur & Executive" https://amzn.to/2ZhpWx2


Jason Wasser Therapist/Coach


Online Tele-Therapy & Coaching 🖥
The Family Room Wellness Associates
Certified Neuro Emotional Technique Practitioner 
🎧Host:You Winning Life Podcast
🎤Available for speaking engagements

linktr.ee/jasonwasserlmft



Muse Meditation- Relaxation Made Easy
Brain Sensing Headbands That Improve Your Meditation

Business Finishing School
Empowering successful companies & families to maximize results.

Wasser's Furniture
Highlighting what's great about buying your furniture from a brick and mortar family business!

Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.
Show Notes Transcript

Life long entrepreneurship is an approach I've been learning more about the last few years.
This week's guest, Alyssa Rapp, is the perfect example of this.
Throughout her career, Alyssa Rapp has not been afraid to ask, Now what?

From training as a competitive gymnast to advising startups and running companies, Alyssa has always been used to working her tail off and looking ahead. By the time she added parenthood to the list, she quickly discovered the need to “hack” the system – find ways to work more efficiently, productively, and achieving at least episodic balance.

Alyssa fell in love with her first entrepreneurial idea while studying at Stanford Business School, and, for the better part of the next decade, ran an e-commerce business called Bottlenotes. Partway through the journey, Bottlenotes pivoted, transforming into a leading digital media company in the US wine industry. From 2015-2017. Alyssa advised startups and private equity-backed companies alike through AJR Ventures; she also taught a course at Stanford’s Graduate School of Business on the Global Dynamics of the Wine Industry.

In 2017, Alyssa and her family decided to move to Chicago where, as of of January 2018, Alyssa was named the CEO of Surgical Solutions by private equity firm Sterling Partners. Within six months, she was named one of Crain’s Chicago’s “Notable Women in Health Care” and made the list for a second year in a row in 2019. Within the same year the company made the 2019 Top 50 Healthcare Companies and Top 100 Leaders in Healthcare.

She is the author of "Leadership and Life Hacks: Insights from a Mom, Wife, Entrepreneur & Executive" https://amzn.to/2ZhpWx2


Jason Wasser Therapist/Coach


Online Tele-Therapy & Coaching 🖥
The Family Room Wellness Associates
Certified Neuro Emotional Technique Practitioner 
🎧Host:You Winning Life Podcast
🎤Available for speaking engagements

linktr.ee/jasonwasserlmft



Muse Meditation- Relaxation Made Easy
Brain Sensing Headbands That Improve Your Meditation

Business Finishing School
Empowering successful companies & families to maximize results.

Wasser's Furniture
Highlighting what's great about buying your furniture from a brick and mortar family business!

Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.
Speaker 1:

This is the you winning life podcast, your number one source for mastering a positive existence. Each episode we'll be interviewing exceptional people, giving you empowering insights and guiding you to extraordinary outcomes. Learn from specialists in the worlds of integrative and natural wellness, spirituality, psychology, and entrepreneurship. So you too can be winning life . Now here's your host, licensed marriage and family therapist, certified neuro emotional technique practitioner and certified entrepreneur coach Jason Watts .

Speaker 2:

Hey everybody. Welcome back. I'm with Alyssa Rapp . She's the founder of bottle notes , CEO of surgical solutions lecture at Stanford business school, adjunct professor at the university of Chicago business school, gubernatorial appointee to Illinois housing development, authority and wife to the 2010 NLB world championship , uh , player, how Morris mom to two children, but wait, there's more in 2008, she was named to inc. Magazine's 30, under 30 , 30 coolest entrepreneurs and the wine industry's top 25 most influential people. And I'm just going to stop there because there's a lot more to say about you, but thank you so much for grabbing . The only correction is my husband won a world series in 1990. I wish you'd want in 2010, but it was 1990, but before my tablet got it. So I guess I'll just read that part, but congratulations . So first of all, congratulations on. All right. I am always hesitant to introduce someone and say, and their spouses , this universally known as to be a little cooler than I am. So that's all good. It's all good. Well , we'll see. We'll see. So I'm because I know I'm very excited and I've been very excited to hang out with this time with you. So before we get into where you're hanging out now, and I know there's also a book that's recently come out , um, let's talk a little bit about how you ended up in this mindset of entrepreneurship before entrepreneurship became the thing. That's a great question. So my , um , I answered the question about how does one become an entrepreneur and a few different ways. First of all, I had great role modeling. My grandfather was an entrepreneur. He had fled the Netherlands during the Holocaust, and when he got back to Holland after with his , my grandmother and their son who did not make it through the war all the way, he was sad and had seen a lot of parallel and was ready to leave those memories behind . So when he came to the U S he started by selling paint , brushes door to door, and he over time ended up figuring out, but the consortium of other paintbrush sellers, where the paint brushes were made, and they've figured out a way to buy paint brush factory. And they expanded that product line from paint brushes to makeup brushes, and later ended up selling the factory and the sales activity to the holding company, parent company for Crayola. And at that time, he also made a pretty strategic investment in a tech startup, but by modern day language, which was called IBM. And so it was able to retire and have his seventies and eighties to himself to travel the world again with his second wife, because my grandmother died sadly at age 50. And so we really, I learned from my old boss that the, that you can always start a new, I talk about this in the book that anyone can become something in America. And so I had that imprinted into my, my life and my life story before I even knew what that meant. And then my stepfather has been in my life for almost 30 years. He is an indomitable entrepreneur in Chicago, real estate developer, and great civic activist, and also created something called the East bank club still to this day, the largest one stop shop fitness club in the country. So growing up and learning his walk-around style of management and seeing him in action, I couldn't help by osmosis, but understand what it meant to start and run a business. And so I think that, and again, those are two great Jewish elders in my life who were great role models. And I have many other role models and mentors who are both women and men, you know, even though different generations and younger generations than they, but I had great role modeling. So I don't want to discount that I was born into a family where it was something that people did to start companies that was door number one, door. Number two is I had great the privilege of a great education. I went to Stanford business school and I knew I wanted to be an entrepreneur. I ended up falling into the wine industry, which we can talk about later. That was not what I set out to do by any stretch of the imagination. But I also was in a place like Stanford. We're in Palo Alto, in the post.com the post dot bomb era of Oh three, two Oh five is a student where nonetheless, the ethos of the place is not , why would you start a company? Why wouldn't you? And I had tremendous education, incredible peers, awesome coaching and great support. So again, I had great role modeling and then I chose a place and was fortunate enough to be a sexual place where it was, it was in the air, they start companies. And then thirdly, I fell in love with an idea. And I think that , uh, that, that process of falling in love with an idea of rightly or wrongly is something that is necessary. I'll be it not sufficient to being a successful entrepreneur. You can't, you gotta believe in what you're doing. And I think you actually kind of have to love it too. Otherwise the shower time and the midnight, you know, reels turning in your brain, it wouldn't be worth it, but all those three reasons are why I think Jason, of why I ended up an entrepreneur, the first go round .

Speaker 3:

Well, there's story that I'm hearing from you is so common. My family, also, my grandfather escaped Nazi Germany on the Holocaust and came here to spend Pennsylvania opened up a furniture store near his later , uh , which is now third generation songs have taken it over . And I became the odd person out, going into the healing arts, and now circling back around through entrepreneur and entrepreneurship coaching. Um, and one of my beliefs is that entrepreneurship is one of the most incredible ways for self actualization potential because the focus from my perspective and , and the people who know me and the people who've listened to this , um , uh , episodes before are about the values based decision making. If I can , and I can't help I work with whether

Speaker 4:

It's an individual, a couple of family, a child, a teenager, or a business, if I don't know what your qualities are, and really the thing that you should say that because I have had that conversation, I can't even tell you how many times in the last several days , um, surgical solutions, I took helm just over two years ago, and it was a classic reboot. It was a classic private equity backed turnaround , where there was a schism of performance, frankly, from what the private equity firm expected. And they got, but what there really was, was a schism of values. So I had to come back in and reboot and reset culture and reset the core values and double click on the mission and really get alignment in the corporate team, which I have done and feel proud to have achieved. And now we have to take it to the next level throughout the organization and continue to make sure it trickles through. Um, but I , I really do firmly believe that core values are whether it's in your home life or in your corporate life, they should be what's driving decision making. It gives me great pride as a parent of two delightful little girls who are seven animals , five when I get the rewarding feedback from friends and teachers that they're so wonderful to have around they're so well mannered, they're this, they're not that way at home with me and how, but at least I know that the values and that coaching and the rubric through which we're raising them is at least imprinting on their psyche and is being translated externally, if not internally, and frankly, same, same culture at a company. We started in the last year, something called leadership lab for our mid level managers in the company. And it's really a , it's really a values based decision making leadership training for module leaders , your training, because that's the kind of leadership coaching I got at Stanford business school as a student, and feel privileged to be a part of, as a lecturer, both there and at booth at university of Chicago, but at the end of the day, it's, I agree with you completely, Jason , that it's the core values that you hold as a team and as a company that should be driving the decision making in the enterprise in the field on a day to day basis. I feel like that's not talked about enough when there's a lot of different aspects that you shared. And I have like all these different ideas running in my mind where I heard a story of a buddy of mine who left college in an entrepreneurship program. Cause his brother went there. He said his brother loved the program. And he was doing one of his projects with a professor and they had to do a business plan. And he went up to ask a question to the professor. And I think the question went along the lines of when you made your business plan for your business, what did you do differently than what we were doing or what insights? And the professor responded like, Oh, I've never owned a business before. And the next day he dropped out of school and he went into financial planning and has become really successful. And I wonder like now rate's 2020. You went to some really amazing schools. You were , were, were around the same age bracket. Um , and I'm thinking back to where I was in 2002 , 2003, working for like nonprofits specifically in the Jewish community , um, where this idea of an entrepreneurship mentorship leadership training was very,

Speaker 3:

Very leadership training was talked about culture wasn't talked about. And I know even today in 2020 cliche, it's very cliche to talk about company culture. Cause it's like throw your core values up on your wall. So when they see it, when they walk in and when they walk out, as long as you have like, you know , a coffee and espresso thing and free snacks and maybe someone coming in once a week of massage, you have a great time . Yeah .

Speaker 4:

And I think that for me, I mean, first of all, I do believe in all those things, I believe that healthy snacks matter, I believe in great coffee and tea in the office matters. And I do try to bring in our friend, Eric, the wellness executive every six months. So I , I I'll check the box and all those cliches, but I actually believe that culture is something that you have to walk the walk of on a much more frequent basis. So what's a better example. We do door dash Mondays because I want my people to have an extra spring in their step coming to the office on Mondays. They don't pack lunch. That's very, you know , sometimes we'll do walk around management where sit down and just chat about life. During those lunch hours, we haven't done a lunch and learn in a while and we probably should, but I'm with someone from the outside, but either even. So we, you know, that's one example, I believe in breaking bread manners . I try to have my team come out to a meal with me at my home or out to the outer Valley with the executive team, at least once a quarter, preferably once every two months breaking bread matters, looking at people through their eyes and having a meal and just having a conversation, some work, some non , but just being human beings, breaking bread, I think is important for trust building and , um , communication skills. I also think it's fun to do things that are non-core to the day to day operations together, like trying to nonprofit events that are affinity core values and, you know, getting people to show up outside of the office and talk about how the work we do in the world. That is his map , that other work being done in the world that matters that compliments our own. And , um, and so on and so forth, recognizing birthdays, calling people when that's been a job well done, actually asking how people are doing through Slack. Isn't a technology tool that we've used to connect our entire 200 plus person field organization to the mothership. And that's a way where I can literally interact with anybody who works for us at any point in time, the stroke of a , of a, of a click. So I think that the lots of things, but it is it's walking the walk. And then from a diversity standpoint, which I firmly believe in, not just because it's the right business strategy because diverse opinions drive better decision making. You know, I walked the walk, just gotta walk the walk, hire properly, hire well, hire diverse teams to take chances on people of all ages shapes and sizes who may not, who have high performance possibility and potential, but maybe not as much experiences . All of that goes into, I think how you can create a culture filled with promise and , and energy. Um , and it's gotta be very deliberate. And it's a day today walking the walk piece of the puzzle. And I also believe you cannot ask people to work harder than you're working . It just is fundamentally uninspiring. And so, you know, to really be out there, cranking is something that I think hopefully over time now inspires, you will say, well, my goodness, if she's out there working as hard, then she ain't ask me to do something. She not doing herself well , then I'll, I'll, I'll buy in and that's not, you know, that's not always the case, but in my life experience so far, that's been the fabric of a startup that I've maintained. I think in all different phases of my career, that piece of it, mission driven, we're all sprinting toward the same finish line in a two to three year timeframe. That psyche is certainly what I think characterizes my approach to business rightly or wrongly. It's probably not right for everyone, right? For every situation, but in the ones I've chosen or that have chosen me, it seems to be the right fit.

Speaker 3:

So objectives are a huge part of it, right? Setting timeframe based goals, breaking it down, actually tasks versus we're just trying to hit a number.

Speaker 4:

It's gotta be measures, dimensions of accountability by when, by whom, for what end and measure and why acting COO of veteran of business leader, Tracy lawn , who had been the president and CEO of the sharper image and then a PE backed company called cycle gear. And now with us, she has this gray line at what is inspected as respected and that's including goals. And we were just having our 2020 goals conversations . It's just got, they gotta be on paper and they gotta be discussed and communicated and wrestled with, and then they gotta be put on the wall next to the desk or put on the virtual wall and reflected upon that

Speaker 3:

It is process . And I'm hearing you talk, I'm so much of what you're saying because the , the platform in which I created this for right , as , as a therapist , uh , who focuses on mind, body integrative health, and then has come around the last three years , um, with , uh, according to my coach, Rick Sapio, who's a capital venture in customer in Dallas. Um, I'm not sure if you're familiar with him, but he has a great program called business finishing school. And that shift from the idea of being like a healer therapist to like, Oh my gosh , I'm an entrepreneur and writing right now happens to be serving in that way. And then that whole servant leadership through , um , however , yeah .

Speaker 4:

And I believe in firmly,

Speaker 3:

So, and ran Stagen , all these. So I've been introduced to all these people through this wonderful network with this mindset of, I'm just a therapist in South Florida in this corner office. And you know, I get to use this platform to hang out with people like you and other people to merge and meld ideas, but everything you've been saying also sounds so incredibly applicable to a family, to a release to a teen it, right ? Like I can break down with you and I'm sure you could as well, every developmental stage of a person's life and apply everything

Speaker 4:

Was better than I, but what I can tell you that I've learned in business, and I certainly believe applies with families and children and spouses and family members is showing up matters, showing up matters, doing what you say you're going to do matters every single time. And you know, I hold myself to that level of accountability. And so then it's, I try to hold my children to it. I am not a perfect parent. I understand there is no such thing. On the other hand, I also try to observe patterns, whether it's people, I manager people in my lives . And I have noticed that with my children. And we noticed this a couple of years ago, that if they got time , even if it was an educational game, like Oslo on the iPad before school, they turn into monsters. It was like the mind-meld was happening. They turned into monsters . So we just decided there's going to be a no screen before school roll . And now we try to have a no screen rule. One is Thursday as a whole, unless someone's traveling and in desperate times desperate measures. And if there is, if we break the rule, we're very clear that it's time bound. I'm very clear. It's a 12 minute, here's the timer. And if there's any drama, when the , when it goes off, there will not be this. You will not have this cheat tomorrow. And I think that it's this whole notion of self regulation and with children, of course, but expectation management. What we do with our kids is helpful tar , but really, really helpful. You know , the alligator tears fly when you got to catch a 6:00 AM flight and they hear you're leaving a foreign come , you know , wanting to hang on to your ankles and leaving at that point, obviously it's pretty heart wrenching. On the other hand, tell him the truth. Mommy's got to go for 36 hours. I'll be back tomorrow night. Or if it's, you know, I will see you and here's what's happening. The 36 hours I'm calling here, the extra special, fun things. I'll have him while I'm gone and I'll see you and it's not easy, but at least it's honest and direct. And here's what the expectations are. And then you follow through. And do you say where you're going to do and with the people at the office, particularly when Jeff , by this notion of managing your values and expectations, it's I find in my experience in business, maybe probably different from my experiences as a parent is that I try to lead with a very, I try to lead professional with a very long leash. AKA , I'm going to be very clear with you, what my expectations are, and I'm going to let you go figure it out. Good luck swimming in the deep end. And if you need me and you need more support, please come find me. And then I'm happy to provide it, but I'm going to assume you are capable of getting it done and you don't need me to micromanage the outcome. And by and large, not always, I have been burned a couple times by that approach, but nine to nine times out of 10, that's been productive approach for me. And I end up getting the best out of people because they say, Oh my God, she believes I can do this. And I've never done anything like this before. Well , Jesus, I better work nights . And we get to figure out how to do this. And I'll come with questions and advice. I'm not gonna start drowning and not ask for help. But I have found that to be a productive way to , um , manage. Whereas with my children , I would not throw them in the deep end, but you know, that being able to, although I got , they could swim, but you know that there are a lot of parallels there . There's no question about it . And I'm thinking of all these, like the thousands of conversations I have had over the last two, three years with other entrepreneurs and other people in the business world, and this theme is running, right? If you put your expectations upfront, here's what you can expect. Here's what you shouldn't expect. Here's what's gonna happen. I literally had this , uh , with a coaching client the other day. And I'm like, what would happen if you started in he's in , um, in a commercial assessment , uh , appraisals. And I'm like, well, what would happen if they come in? And you say, what's the number you think you're getting from this appraisal? Cause they might tell you like , it's an a million dollar thing and they're really only going to get six. And then when they get the number of six or five, they're like really pissed off at him. Right? So I said like, start asking them, what are you actually walking ? I think that the negotiation strategy of , and there's obviously two schools up there . I've never put the number on first because you don't, if you're leaving value on the table, then there's the other point of view, which is, this is best and final. I'm not playing games. And you obviously have to mean it just like if you say, if you hit your sister and you're going to time out and have to follow up, we use that strategy very recently with a couple of trickier scenarios, which was, listen, I made you an offer for X was X . You came back and asked for three X. And I said, no, no, it's actually X best and final or X plus 0.5 and that's best and final. And then we're walking and I meant it and was prepared to , and two different strategies. One with someone exiting the company and one of the major customer that we were renegotiating pricing, I actually meant it. I had gotten to the point where they were asking us to do things that were on standard for the business and I , since best and final take it only , even if you leave it, I'll be devastated and that's life and they took it an hour done . So my point is, is that I think that that notion of running some of the charade, I don't have a lot of patience for it, to be honest with you. But running this charade is something that I firmly believe is beneficial to negotiation. And , and it is counters philosophy , negotiation, strategy, the zone of compromise and anchoring and start with something that, you know , you never did the first time or not . And I've taken those courses. I have learned from those wise people. And I agree with that strategy in some select cases. And then there are cases where there's downside risk , like your client, where if they piss off the customer and that person might walk in, they might not get anything so better to expectation manager up front and just say, listen, this is not exactly. He's not even doing an assessment. This is before they've even done an assessment on the property. If the client coming in and saying, here's what I think it's worth. My client has no clue and it may be worth more. It maybe worth less. But if I'm challenging him to say, I just want to let you know, just because you think it's worth it because it's 10 blocks away from another property, that's worth that money. It doesn't mean it's zoned or whatever . My friends who are in their forties dating, I'm not going to be, I'm not going to lie. I mean, one of our very close guy, friends and I have a very close friend, who's a terrific person. We both think he's great and should be a great fit for someone. But he's like 48 never been married. There was some family tragedy 10 years ago, which caused a little bit of a time. I call a time gap. Cause it was diverted his focus to his brother, his late brother's family, et cetera. But he's like this great guy alone in California, running a family business, doing really well. And I have two comments to him. One, no one's coming down. The chimney Santa doesn't exist for dating. I'm not going to, first of all, with any children, did my come across this podcast to too .

Speaker 2:

Don't keep making the same mistake you made for 20 years. Like if you haven't met the right girl at the bar for the last 20 years, and you're a Dartmouth undergrad with a Berkeley law degree, probably not going to be the right girl to bar and year 21 and door number three, cut your losses sooner. If you are seeing warning signs, people show you who they are in a relationship real early real clearly. I've seen it in business and it's hard to pay attention, but it's, you know, shame on you. If you don't, especially as you get older and wiser. So tigers don't change their stripes, at least not very quickly, right? And we tend to make the same mistake, not five or six times, but 20, 30, 40 times in a row before we change a pattern. So let's go back. Cause I know our time is limited, but I want to go back to , um, to why notes and how that happened and how you ended up there. Um, and then taking it a little bit more into the context of your personal experience of female entrepreneurship and bottle notes was something I started while at business school. And it was an idea that came out of a whole amalgamation of different courses and studies and an internship and things. There's a great chapter on it in the book leadership in my facts, she can get on Amazon. Um, and the, and the problem I identified in the marketplace was that the internet was being insufficiently utilized to match people to products in the old three to five era. And what better product is one as opaque and complex as mine and the next generation wine and consumer was also on the rise demographically and buying more wine at higher average price points. In our average quantities in the boomers. Now that's shifted in the last year. So now we're 15, 16 years later, that's shifted. And the share of buzz is being absorbed by craft beer and canned canned spirits and sell hard sell and all those and cannabis products, et cetera. So it's a much different world, but then rolling back 15, 16 years , um, it was amazing to say , uh, it was that millennial consumers were drinking more wine that are higher average price points and higher average quantities and the boomers. And we're not feeling connected to buy the wine enthusiast or food and wine or all these sort of baby boomer friendly, high brow, low , uh, approach , uh , low approachability platforms . So we were trying to blow the lid off the industry, be the wine enthusiast or food and wines . The next generation we started as the Netflix for wine as an eCommerce play great chapter in the book, probably one of the best and strongest on pivoting versus quitting or rate to pivot our strategy from , um, e-commerce to media because of a big regulatory shift. But , uh, that, that was a very organic change where we could have put up the white flag or pivot pivoted . It was a hard, hard, hard, hard thing to do, particularly in a week given the financial crisis, but we got it done. And , um, and so really that was a very explicit lesson in sticktuitiveness grid, a dog, you know, dog , entrepreneurial spirit, all the things you hear about and in the journey of an entrepreneur, but for us, we were also really focused on the customer. We were always focused on solving a problem for the customer, which was initially getting them wine tailored to their personal tastes, using patent pending matching technology. And over time, as we pivoted strategies, helping educate and entertain them about wine in ways in which they wanted to be educated and entertained , email newsletters, large scale interactive events. We toyed with an app. I wrote my first book around the world, 90 steps, name, that tune we were educating and entertaining the next gen and then brands wine. And non-wine luxury brands were advertising through us to reach our audience. So that focus on what does the customer want and giving them what they want when they want it, how they want it is. I mean, that transcends industry. And that was one thing we did really well. I'm thinking like there's like breaths of like you focus on a niche and we chunk it down, which I'm done. They always talk about this. And some of my mentors have like, you know , what is that? That at the end of the day, what's the niche and the niche and then are in the niches badly , right? And the crumbs left on the table, I'm in a major industry. If there you just solve that one problem, especially if you're focused, excuse me. What I found the hard way is that what's hard to do is figure out what not to do as much as what to do, right. An entrepreneurial add is one of the things that's really hard. It's really hard not to chase the new shiny toy though . That was a mistake I made the first time. I didn't, I was focused on pivoted , but I wasn't willing to let go one or two legacy products. I just couldn't let go. And they were great ideas and they could have been businesses of their own, but I don't know if I go as far as called entrepreneurial entity , but entrepreneurial unwillingness to let go. That was hard. And it's very real and I've gotten much more disciplined and also much more discipline . Now in that I have made some angel investments every time I've made one. I literally, I mean, when I tell you, I literally write it off in my mind, I don't even think about it. I'll do anything for the entrepreneur. I want to be helpful. The second I written that angel investment check , I pretend like it went up flames because no matter how good the idea, how smart the entrepreneur, it's a nine out of 10, it won't work and I'd be happy to help and hope it'd be the one out of 10, but I don't think about it. Whereas, so I do that with a very small piece of my personal portfolio. Cause that's not a strategy, good investment strategy to write checks. And like I'm on fire. Alternatively, with seed stage investing in venture, I tried to take a more pooled approach where my family and I have a couple collective investments in seed stage funds, where I have really smart people who might love and trust, canvassing the strap , the land for their particular strategy and niche around seed stage investing. And while my upside will be capped because we're part of a consortium and a fund, my downside risk should be a little bit lower because professionals are looking and vetting, et cetera. Um, and that's been a way to sort of stay involved without bleeding checks on fire as often. But , uh, it's, it's the thing I look at when I look at anything personally and directly or indirectly through these funds as they come through is that narrowness of purpose and focus because that focus that clarity of purpose,

Speaker 4:

You know, you can't control for industry dynamics all the time. You can't open, you can pick a big enough industry as we discussed, but you can't, there are things you can't control, coronavirus, et cetera, et cetera. But what you can control is how focused you are in your strategy and that the more focused the better in my mind.

Speaker 3:

Exactly. Yeah. There's so much good stuff there. And I've like 14 different things that I want to ask and share with you. Um, but you were talking about, you know, the numbers and being laser focused as a female entrepreneur, the one the numbers are finally growing finally shifting and changing the landscapes changing before we're having a pre conversation about , uh, about billions and the female billionaire entrepreneur , uh, the season what's that journey been like specifically for you, right? You already came from this background, you were already supported. You already went to a good school where some of the things ,

Speaker 4:

Oh , listen, I mean, I was trying to make waves in a male dominated industry and a male dominated, two male dominated industries, tech and wine. And I was doing it creamy too. So every me too story you heard, I lived, it was awful. I looked at all. It was ridiculous and demoralizing and absurd, and it inspired me to pull together great women venture capitalists from Silicon Valley who were close friends and panels on at Stanford business school on what it's like to be willing to venture capital cut, to present it . And it has inspired me to teach a new class at the university of Chicago booth business school on women, as CEOs, investors, directors, and board members like that's coming up next month. Like I'm walking the walk, but in between those things, you know, these seed stage investment funds, I mentioned to you the strategies for one of them bleed out, capital's invested in women in diverse , um , CEOs impact engine double bottom line impact through the activities of the firm plus diverse leadership teams, Corazon capital funded by a dear friend of mine, San Diego. And they do seed stage investing, but he's got an extraordinary track record on diversity. So then there are others and other classmates started selling called Jane VC . I'm really excited about directly invest in female entrepreneurs myself. So I think that the numbers have improved me too is me too. There's a lot lower tolerance. There's a lot more scrutiny and there's a lot more investment by women in women and by diverse, you know, investors in diverse leadership. And yet I think about my non career and I think about my own career and private equity. And I think about my own aspirations being on public company boards today, you know , hopefully not 20 years from now more like five or 10 and only 7% of those public company directorships roll over every year seven. So it doesn't matter if you've got the perfect resume or the great network and you need all those things are necessarily not sufficient. You need the openings. And so I think there are pluses and minus district two , two regulatory strategies that mandate diversity, I really do. I'd just love for companies to do it cause it's the right thing to do. And I think Goldman Sachs recently set a pretty great precedent on that. So I, I'm not saying I think it has to be regulated. In fact, I prefer for people just to do it cause it's the right good business practice to bring more diverse viewpoints to the leadership table or table executive team, et cetera. Um, but you know, I, I lived in an era where, I mean the stories I could tell you would, you know , knock your socks off. And I think that I'm grateful that I got through it relatively unscathed. I lived some of that stuff the hard way. I was super lucky and feel very blessed that I was going with my husband through that whole era. We weren't married told , you know , piece of that time, but she lived that movie with me and he had my back and he know I was sounding board. And I think that having a great partner, irrespective of gender is an incredibly important thing to have in entrepreneurship. I think some only road. Um, and I feel very lucky that I, how was my person throughout the whole thing? I , I don't , I'm not that I wouldn't have made it, but it wouldn't have been half as fun. And it's not to say it was all rainbows and butterflies for him or offs in that pace . It's a hard thing to do. It is a hard thing to do, whether you're Mark Zuckerberg or me, it's a hard thing to do. And people underestimate because of, you know, fantasies and shows like billions, which I like you love. And because of the biases in the popular press, we focused on the unicorn outcome, but you don't focus on what it takes to get there. I mean , it's hard. It is hard. Some have it easier than others, but it's hard. And so I think that that's a piece that's under sung and that, and it's that much harder if you know, your ginger Rogers doing it backwards and Hills . I mean, that's just the reality,

Speaker 3:

Right? And then you have, you, you have a Sarah Blakely, you have all these different right , who are changing this face, bring on in the experience of what's going on. And cause I love , um, I did a program build your life resume with Jesse Itzler, which is one of his online , uh, these and they're very much welcomed. Like the community's very much welcomed into their, their home life. Cause they show like this is how we do our work life balance. This is , this is how so I'm really curious for you where you married professional athletes , where you're incredibly driven. I'm assuming he's as incredibly driven to become an elite athlete at that level. Um, how important is that in relationship dynamics from your experience? All right . Again, I know you can't speak from everybody in your, like how much of that was something that you were looking for and um, and what have been some of those pros and cons of having two people who have been,

Speaker 4:

You know, I think I chose someone who was an athlete cause I was at a different sport in a different time and a different era and league, but I was very serious gymnast and dancer from seven to 17, like, well it's 21 through dance three hours a day, six days a week. So the irony is I keep the joke that I probably, you know , cranked harder and more dedicated fleet growing up. And he did , although he obviously is an extraordinary talent and I deeply admire his talent and his drive and his dedication. Um, so that those are all pieces of what I knowingly or unknowingly chose. I definitely think that being an athlete is core to who I am and it's core to who he is. And those are big pieces of it being on a team matters to both of us. And I view us as a, we absolutely unequivocally are different. I'm an extrovert, he's an introvert, blah, blah, blah, blah, blah. So the opposites attract piece. And then there's the also piece of it where we have very, very, very complimentary values. There are very few times that our values are out of step on anything. And that is also pretty core because it means that, okay, he's the introvert I'm, Yesha , we're going to squabble about how many social outings we haven't given one that is a squabble. How often do I have to drag him out? But what we're never going to squall about is what to invest in, how to spend our money, how to family first, we're not doing none of that stuff and we are just in lockstep on all of it. Well, yeah, I think so. I mean, I do think so. And so I think that, you know, the grit and the ability to keep swinging, I dedicate the last chapter of the book, my book, leadership and life facts to him. And he has reminded me in those entrepreneurial years and present tilts in hind thinning. And the third hour you have to keep swinging because you never know how it , the tide may turn. And that I learned myself on my own prior to our relationship, but has been wonderfully reinforced through it. And I think that, you know, so the values and the kindred spirits and souls I think is really matter managing that we're very, very, very different people were also good Midwesterners who really funnily above all else value hard work. And that I think is also pretty important. I think people have many different types of marriages that work in it as far. Be it for me to comment on anyone else's, we all know the politics of people's personal lives or , or a personal and be complicated. But , um, I do know that the old adage of pick someone, you know , with whom you can never run out of things to discuss or there's enough overlap to have shared interests, but enough, the Venn diagram has an lacking an overlap enough that there's always, I always feel like I could learn something from him. And I think he probably feels the same way because otherwise, you know, life is long and you know, at the end of the day you got it, you got to still connect. And I think with kids , um, you know, my husband was married once before he had four. We met and he has children from his first marriage and his eldest child is someone whom I have a great relationship and, and that's also been his own journey. And he was also very, very open to me having my own relationship with his oldest and grateful for the input and role I have had. And that helped right . That helps to, to, to make it all work. Cause I have a stepfather with whom I have a wonderful relationship. He's been an extraordinary to me. And so I was hopeful that I would be able to provide that role in some way, shape or form to any of his children. But it's life is complicated and postmodern family life is complicated. It ain't easy being green. You just gotta keep on keeping on. And , um, and you know, two little girls is precocious and delightful as they can be here. A lot of work juggling with the work in the marriage and the civic activity and the teaching and the rest of the book. And , um, and so it's, you know, I don't, I guess a good closing comment will be one thing I get asked about the globalized what's favorite hacks since its leadership in life hacks, a hundred tips for living, living your life, more efficiency efficiently with greater impact. And I think the best hack I've got that encompasses both business and family life is episodic versus daily balance. I cannot , I do not try to get everything done in a given day because it would be a colossal failure and like this week, how's it spring training, which is fantastic for business, which is fantastic because I don't have to, that is not miss , but it's not, it's easier to balance too . And I'm not also trying to satisfy that stakeholder. Right? So this week is about being a mama CEO like that's this week and doing a little bit of PR around the book like that's this week. And I try to nail Tuesday callers a day and do something for 45 to 60 minutes every day for myself. And that's how I try to, you know, put your own oxygen mask on first, take care of you so you can take care of others. And then obviously really show up and be present for my kids and my career this week. And then there'll be the set . And then, and then the episodic balance case in point, how has a colleague getting married? And he really wanted me to go for 24 hours. So we're going to punch out and go to Boston, do a Boston run for 18 hours Saturday to Sunday. And that'll be tunnel of Nazi healing and not bombing , but I'm going to like show up and be a great way. And that's , and so it's , it's so over the course of seven or 10 or 14 days, I hope to achieve or be everything I need and want to be W2 those stakeholders, but it's not getting done in a single day. So then before I let you go, the last question really related to that is what's one self care activity that you think you , that you may have experienced or seen other entrepreneurs lack . I see. And I see this entrepreneurs are not, I see my friends who are in very, very busy work phases of life, married or not kids or not, not doing that 45 minutes a day for themselves. Like one of my best friends in the world. It was superstar surgeon. She's fantastic. Um , and there was a period of her life where she just was not giving herself for 45 minutes a day. And for me, that's working out for her. It could have been meditating or you know, extra sleep right now . I'm not here to tell you what your one thing is, but she was just getting depleted. And I said, listen, the irony is you need to take the time for yourself, put your own oxygen mask on first and know for , and I've been working out too. It wasn't even how you look at how you feel and you got to take care of you. And so I think that not letting it go. And I'm not saying it's easy. I hate 6:00 AM flights. You know, they kill your, you have to three , three in the morning, you get the workout in which I do sometimes. And not others. Like that's hard, but at the same time, you know, don't want perfection , be the death of progress. Just take care of yourself a little bit. Even if you can't, even if it's a 10 minute meditation at the 45 minute workout, God forbid just do something to take care of you because clock keeps turning the time keeps you don't get the time back . So, you know, I think that's the take care of you. It's easy to get lost in the, in the, in the dream and in the grind. It's easy. Cause I remember, you know , my first startup, you know, you turn on your computer, you know how long we're living together. We didn't have kids yet turn on this exam. Then you get sucked in. And before you start your day, you're running pants and it , 11:00 AM. You'll get of it . You're virtually in your gig economy working on it with or taking a break. And you're like, okay, well I'm gonna take a break . I'm going to work on that here . But by taking the email, keeps calling in the phone, keeps going, Slack keeps going and it's, it's easy to not do it. And you just have to carve out the time, right? It's like the text fast or a Sabbath or whatever. Right . Space at different communities who have that's created her so important again, that's also scheduling it in rhythm and ritual . I schedule everything and that's, I think the ritual is your phrase. It's a really good one. That's the that's that's got happened. Jason's gotta be ritual then it's not, it's not something that's moveable . Just like a call with your executive team. Wouldn't be move . It has to happen. And this is when it happens. It happens. We schedule around it and it sort of sacred time. Like you have to shower, you have to have your 45 minutes. Awesome. Thank you so much for having me . And I applaud all the great work you're doing coaching people. Like they're lucky to have you. Thank you. Thank you. And everybody , please, please, please check out the book Amazon. It was right at the main place. You can get it right. It's leadership and life hacks and check it out again all the above. Awesome. Thanks so much for having me so much.

Speaker 1:

Thanks for listening to the you winning life podcast. If you are ready to minimize your personal and professional struggles and maximize your potential, we would love it. If you subscribe so you don't miss an episode, you can follow us on Instagram and Facebook at Jason Wasser , LMF T .