Good Eggs, Good Break and Teaming Up with Gretchen Rubin: Interview with Anne Mercogliano

March 12, 2021

By Matt Miner, MBA, CFP®

Anne Mercogliano is back for her third podcast appearance with another update - she went into business with my favorite happiness author Gretchen Rubin! In an earlier conversation Anne said, “2020 throws a lot at ya.” That’s true, and in the midst of “a lot”, Anne got a lot done.

Anne Lays out the plan and drops value bombs with wit and grace. She doesn’t say it in so many words, but Anne provides a blueprint for treating your career like an entrepreneur.

  1. Show Up Fearless

  2. Engineer your own Layoff

  3. Launch a Media Business with Gretchen Rubin

2020 Throws a Lot at You

Whether coping with professional challenges, gyrating markets, the need for childcare in a pandemic, or just the fact that Costco is out of bacon, this is a difficult year for everyone. 2020 is teaching us to hold our plans with an open hand and be ready to adapt.

Addition by Subtraction

Anne sets the table for us, describing changes she encountered at Good Eggs as the pandemic began to bite. Her employer found themselves with “scaling issues and the need to preserve [their cash] burn”, meaning the business wasn’t growing as fast as they wanted and everyone saw the importance of not running out of cash – always a key consideration, as I discuss here.

With Good Eggs focused on serving organic demand rather than driving fast growth, Anne got to be part of the decision to continue to work in that environment and lay off members of her team, which is heart-wrenching, or to take herself out and preserve some jobs of people she had sponsored up ‘til now. Anne took door number two.

Raise Your Hand - and Do the Work

Anne points up the importance to not only propose ideas, but to lead implementation. Ideas are like [opinions] - everybody’s got ‘em. Execution - the ability to take an idea, craft a plan, gather resources of people and money, and get a project across the finish line - that’s where the money’s at.

Anne Mercogliano for Mayor of SF

Anne recommends having “five things you want to be”, because having only one goal leads to analysis paralysis. Then, on your way to your goals, embrace the tension of having a destination in mind and being flexible in how you get there.

You Can’t Do Everything at the Same Time - but You Can Do an Awful Lot in a Lifetime if you Don’t Get Lazy

“Overnight success” comes after ten years of toiling in obscurity. Social profiles, resumes, and biographies flatten a lifetime of effort and experience and obscure the sheer amount of time and work required to accomplish anything worthwhile - raising children to be successful adults, building a career, or launching a business, for example.

Anne recounts a women’s event at Twitter with Madeline Albright where one of her colleagues asked the former Secretary how she accomplished so much in her life and work - Albright reflected that life has many chapters. What the world sees as an accomplished life happened as Albright followed a plan over many decades. Building a life and building wealth are pretty similar that way.

Anne’s Recommendations

Super Pumped - The Battle for Uber

Tender at the Bone

THI$ Is Uncomfortable podcast

Connect with Anne on Twitter

FuquaVision

Bohemian Rhapsody, Fuqua Style.

Remember the E*Trade baby commercials? Fuqua had it’s own take on that, too.

Here are Shane and Anne, too. With a little effort and apologies to Flight of the Conchords, you can even find me in the archives - not that I’m suggesting you try! Some content is best when it remains obscure.

TRANSCRIPT

 

[00:00:01] Matt Miner: Today's show includes three conversations with Anne Mercogliano. We begin with Anne's exciting new work with Gretchen Rubin. Then we discuss how Anne designed her exit from Good Eggs to focus on family and board service through the middle part of 2020. At the end, we hear from pre-pandemic Anne and me about her post-MBA career and work at Good Eggs. These interviews were recorded in February 2021, July 2020, and January 2020, respectively. Hey, and welcome to the Work Pants Finance podcast. I'm Matt Miner, your money guy. Work Pants Finance is the show for MBAs, entrepreneurs, and other professionals who want their financial plan to work as hard as they do. This episode is Good Eggs, Good Break, and Teaming Up with Gretchen Rubin: Interview with Anne Mercogliano. You can read more at workpantsfinance.com/8.

[music]

Now here's today's money guide quick tip. Sometimes life is a matter of addition by subtraction. This may involve simplifying your schedule, decluttering your garage, or executing a career change in the middle of a pandemic. When change finds you, even if the change is painful, look for the opportunity it presents and be ready to act in the midst of disruption. Self-awareness and planning are key skills that help you be ready. Also, sometimes life is a matter of being silly in front of a camera. I mentioned FuquaVision on today's show, be sure to check the associated blog post for a few favorites of mine. I don't know how well they translate outside Fuqua and MBA culture, but they take me back to a really fun time in my life.

[music]

Anne, as I planned my new show, including rereleasing our content, I pulled up your LinkedIn profile and saw that you have a new job, which didn't surprise me. But when I looked at your organization, my jaw hit the keyboard. I was like, "Anne is working with Gretchen Rubin?" Just like the last time, I got ready to release your show, I wanted to interview you a third time. Welcome back to the Work Pants Finance podcast for the first time and our third conversation together. In our earlier conversations, you've given us a really great descriptive biography, but I wonder if you could just provide a brief introduction here.

[00:02:16] Anne Mercogliano: Sure. Excited to be back again. We know each other from way back in the day at the Fuqua School of Business, but I have been in the business world since in management consulting, a startup in marketing, and now co-founding a really fun new media company with Gretchen Rubin.

[00:02:34] Matt: That was just so striking to me. For the three people in my audience who aren't familiar with what Gretchen Rubin's all about, can you give us the short version of what she's up to and what you're up to with her?

[00:02:46] Anne: Sure. First and foremost, she got her start and really what her platform is, writing a book called The Happiness Project. Absolutely incredible. I will say, the only time in real life we have met was at a book signing in 2010 in Boston because we've done this all digitally in this new 2020 world.

[00:03:04] Matt: You were there having her sign her book or was she signing your book?

[00:03:09] Anne: She was signing her book. I was just an overworked management consultant at the time and looking for advice on how do you think about actually and practically bringing more happiness into your life? She wrote that, and she's gone on with a bunch of different series. Her main promise is practical solutions for being happier, healthier, more productive, or more creative in your life. Really, the idea there that I think is really compelling is it isn't a destination, and it is really a constant process. The second piece that I think is really compelling is also this idea that she thinks about, it's not just one way, it's not there's only one way to do this, figure out more about yourself.

She gets a lot into some of her future books, like The Four Tendencies or Better Than Before on how do you actually think about behavior change, because that's really the key to thinking about being happier. What are the ways that are going to work for you so that you have these practical solutions? That's her in a nutshell. She also has a very successful podcast of her own, Happier with Gretchen Rubin. It's taking her as an author and this personality into actually founding her media company because I think what she has to say and what her thesis is, I think the world really needs it and could benefit from it, from bringing it to an even bigger stage.

[00:04:30] Matt: I think that's absolutely true. I think after living through 2020, we can all afford to be happier. Anne, you described your work as taking what Gretchen has done and bringing it to the world. I wanted to ask how you ended up in this role. This is not a job that's posted on LinkedIn. Tell us the story.

[00:04:48] Anne: Fun fact, she actually did put the call out there into the world on her podcast, which I think is really amazing. But the personal connection on how we had our first call and started talking is an old boss of mine when I was at Twitter and a mentor who was helping us while we're at Twitter, Kim Scott, wrote a book called Radical Candor. My old boss Ross was the co-founder of that company as they took that forward. These are these people in my life, I would call them my personal board of directors. I would always go back to them.

In 2020, Kim was actually working a lot on how she takes her book, Radical Candor, to the next step and actually coming up with some really innovative ways of teaching managers new ways to do this in a world where we didn't have all-day offsite sessions and reached out to me on thinking about her growth strategy. Kim being the amazing mentor that she is, thought of me when she was hearing about Gretchen looking for this new role and connected us. I feel extraordinarily lucky that it comes from mentors who are willing to advocate for you and just say, "Hey, you should go explore this more." I am very lucky that it came from those connections and just staying in contact with people who really have always been there for me.

[00:06:02] Matt: Just goes to show how important those relationships are, and no surprise to me that folks are interested to continue to invest in you, Anne. I appreciate you sharing that story. I don't know what you are free to share externally, but I can never take my MBA and organizational thinking hat off, so I wonder if you could tell us a little bit, what is the business and team like that you and Gretchen are building together?

[00:06:29] Anne: It is fun because it really is building from the ground up. I joke that the first couple of months was Anne putting on her green visor and getting into QuickBooks and Gusto and setting a lot of the organizational pieces that you need, but really, I've been extremely lucky because I actually hired a woman who I used to work with before to run all of marketing. As we're thinking about what are some of the technical, the engineering, and product strategy side, how do we bring in more people from that side of the house, she has a great concept and she has already many channels that she's doing really well in.

How do we actually pull all of that together so that they talk to each other so that we're able to essentially take this idea and put it into different formats that are going to engage with everyone who is interested? I always say, repurposing content, it's the feature, not the bug. It isn't just taking the same thing and tweeting it out and then recording it on a podcast, but what are all the different ways that people want to learn? Everyone has a different learning style. Everyone sometimes needs to hear things in different formats and different ways. Really thinking about what she's doing and making sure that we have a variety of different media properties that we can take that and bring that to life.

I also think it's really interesting because she's all about practical solutions. A lot of the next year is building out ways that you can follow along. It's taking it from potentially her being able to offer you ideas and practical ways to actually engaging with her. There is such an interesting world that you can think of with interactive in apps or web experiences. I think it's the next phase of content, to be a very media buzzword, of all this, but it's the next ways that I think interactive content is really going to be a place that people want, and once they experience more examples of it, are going to really demand. She has the perfect thesis to bring that to life. That is the fun part is, bringing a little bit of Silicon Valley's speak into this media world, but how can we actually create this platform for her?

[00:08:33] Matt: It's so exciting, Anne. I think that we could easily do another 45-minute show on it, and maybe we will after you've been doing it for a little while longer, but I wanted to just bring people up to date, and I really appreciate you coming back on today. Is there anything that we haven't talked about that you'd like to mention? Any place you'd like to direct people to follow up at this time?

[00:08:53] Anne: If you're interested in Gretchen, I highly recommend checking out gretchenrubin.com and checking back there because there's lots of stuff we're building in the background. Then the other thing I just want to give a shout out to you is, I am extraordinarily compelled, as you can tell, by what she's working on, which is just practical solutions and thinking about ways to be happier. That's also the main driving force of why you're doing essentially all the work that you're doing. I just also want to say, all the work and how you're thinking about how finance and life and all the ways that you can find what works for you is going to lead to much more success and happiness. Spend more time investing in Matt Miner because I think you're also doing some really compelling things as well.

[00:09:35] Matt: Anne, thank you so much for those kind words. I do think that it's all about figuring out how these things fit together, and then at the end of the day, like what you are doing as you bring this as a media business, what Gretchen is doing with her content, what I'm trying to do with my content, is just help people. That's rewarding and fun, and I think we'll all just keep on. Thanks for doing this second addendum to the first interview. I think they've only gotten better.

[00:10:02] Anne: Thank you so much. I'm very honored to be on again.

[music]

[00:10:07] Matt: Today's show is brought to you by the Work Pants Finance team, and we'd like to give a shout-out to the La Pointe Foundation, a 501(c)(3) nonprofit founded by my good friends, Caleb and Charlotte Whitmore. The La Pointe Foundation is doing amazing work in Haiti, focused on education, sanitation, healthcare, entrepreneurship, and food. You can learn more and give at lapointfoundation.org. That's L-A-P-O-I-N-T-E foundation.O-R-G.

This is the original interview recorded with Anne in January 2020. Lots has changed since then for Anne, for me, and in the world, but I think you'll still enjoy our conversation.

[music]

[00:11:01] Matt: Anne, it is so good to have you with me here today. Thank you very much for taking the time to get together.

[00:11:06] Anne: Thank you so much for having me, Matt.

[00:11:08] Matt: We've known each other a long time, going all the way back to business school. You're someone who I've always enjoyed visiting with shared a lot of fun times there from some late-night adventures to Duke basketball and maybe some learning along the way. It has been my pleasure to just watch your career from afar. You return to the west side of the country, where I'm from originally, and we've been pretty stubbornly in the south and the Midwest. I've really watched you build a career at this interesting meeting point between business and media and marketing very generally, and you've done some neat stuff. To kick us off, and so my listeners know who you are. I'd just like to hear the version of your story that you're willing to share with us.

[00:11:53] Anne: Sure. I am a navy brat, but I like to claim Philadelphia as my home, it's where I spent most of the time. I went undergrad up to Massachusetts and I will talk about this migration pattern of going straight from there out to the west coast. I thought that I was going to be a lawyer actually. There is another universe, Matt, where I worked for a law firm. I thought that was the best in. I took the LSAT I applied. I got in. Actually, at the last moment I started working on this really interesting project with a woman at HBS because we were doing this thing called the opt-in revolution, which was based on there was a huge New York Times article about the opt-out of how do you think about On-Ramps and off-Ramps for women and just all of diversity in careers.

I was doing that. We wrote a paper, and this woman was like, "Hey, I want to study what you're doing." She said, don't go be a lawyer. She said, "You have way too much of an entrepreneur." It was very funny pulled me aside and it affected me a lot. I pulled and said, "You know what, I'm going to defer for a year." I am always proud when I sit on like women in MBA panels where I'm like, you can be a total hot mess and apply at the last minute to business school and still get in. I was like, "For the one person out there that doesn't have it together. Don't worry you as well can still live the dream." [laughs] I took the, let's see, I say the GMAT Thanksgiving to Christmas took it Christmas Eve went home, saw my parents wrote a bunch of essays and [unintelligible 00:13:17]. Then was lucky enough to end up at Duke.

[00:13:22] Matt: I think one of those things that, that highlights is like, you never get anything without asking, right? If you want to do something, you just got to try.

[00:13:29] Anne: Totally. I always say I chose the liberal arts degree of our MBA, which is going into consulting. You don't have to really choose anything. You can be well-rounded and by that, I always say consulting really is the best cocktail conversation. You're thrown in and it's, I spent four months understanding what could be the big box retail strategy and differentiation by channel for asphalt roofing shingles coming out of a very well renowned building supply manufacturer in the Midwest. Then after that, I worked on Native American casino gaming expansion and different ways that they could think about the world of online industry and then a hotel. It was the [unintelligible 00:14:07] on days of 2010 and they were like, "We should have an app." That was how you would jump from different case to different case.

I loved it. I thought it was actually a second education to my MBA because you just had to come and soak up as much knowledge as possible and then really help them just cut to the quick. That I always say was some of the best training. Essentially did that. I was really lucky because I had a partner who I loved that I worked with at L.E.K, who actually decided that he wanted to leave and join a friend from business school that he knew who was from McKinsey. They were founding an internal strategy business group at a company called Hiva, which is a big one of those big media holding companies. The Korean agency that I sat at was Arnold Worldwide in Boston. What they were doing was typically on the consulting side of the house, I'd come up with the big here's your five-year strategy, we'd handed it as a deck.

Then we never saw the fruition, but they would take that if it was a marketing strategy and then take it over to their agency. There was always that gap in between. It was how can we do that work and then directly feed that into actually like a media plan or a creative plan. Lots of fun. Let's see, Ocean Spray, the bog, people worked on that, and the insight there. Cross pens, which I always thought was fascinating on how do you make pens relevant again? How do you think about that as a gift? Tons of airline work, and yes, a lot of fun. I was also very lucky at the time I met my husband in Boston. He was ex consultant as well and still there. We decided to get engaged.

We were not from the area. We moved west back out to California where San Francisco just gets into your heart and your skin and you just miss it a ton. We moved back out here to the bay and I decided I wanted to actually leave the professional services side of thing and get to build. Not just the deck, but actually get to build with my hands. I enjoy the organized chaos of trying to get it done. I was lucky enough to have a connection from the consulting world that went in to be the COO of a company called Trulia. Now owned by Zillow. They hired me to think about demand gen and I always say it's one of those things when you're leaving consulting world, you're like, "Sure. I don't know what that is yet, but I will gladly take that on." It was a lot of fun.

It was coming in and saying, how do you bring order to chaos? How do you going to get them ready? They were going for their IPO that year. It's like, how do you get them in tip-top shape? Then really lucky enough and I still think about this as one of the most fortunate times in my life was Twitter was just on the rise. They brought Dick Costolo in, who was basically saying we have to monetize this business and bring this public. At the time, it's so weird to think back. You couldn't buy a Twitter ad on there. You had to call somebody up and they would give you your Twitter ad and you had to be Nike or Pepsi or something. They needed a self-serve platform. They needed somebody to do it for all small-medium business.

Actually, they recruited me over and I jumped at the opportunity, but I was one of the founding members. We built that from essentially it being in alpha and trying some prototypes all the way to opening up globally and just about every country, but China because they're not there at the moment they're blocked. Not every other one. That was build that global business. It was amazing to have teams in Tokyo and in AMIA and Latin America. I was also fortunate, I would say this is really key part of my life because that's when I also had my daughter, and so tons of fun. When you think about all the offices and all of your directs and they want you in each office at least once a week per quarter, you start to add that up and you're like, well that's a quarter alone when you start to realize all the different traveling.

I decided to step back and say let's do something a little bit smaller but at the same time, I wanted to take on more of that responsibility. I went to the true teenier startup app and it was a company called IFTTT: If This, Then That. When you think about that, it was an amazing geeky. You could always find somebody writing about it on Product Hunt or HackerNews or community out here of especially people who love to play with the internet of things was just becoming a thing back then. Literally no monetization plan. It was the absolutely quintessential make thing question mark profit. They hired me to do, I always called it Anne and 39 dudes because it was just engineers and me. They hired me to think about their marketing.

What is their positioning? What is their monetization plan? Actually, launch the business side of the house. That was a lot of fun. So does the marketplace essentially have things like these small little internet of life balls, but like life X or something big like Phillips or, we worked with things like Honeywell. There's a thing called Nest, what do we do? How do we get into Nest? It was a lot of fun because it was also the time when Google and Alexa were starting to build their verticals and it was how do we actually make it so that anybody could plug into those and also they hadn't made out their ecosystems yet. It was great to build that business and really bring order to chaos. I really enjoyed that piece.

Then I've always loved cooking. That is my passion on the weekend. It was actually the former CEO of Twitter, Dick Costolo, was mentoring the CEO of Good Eggs. He said you should check out this woman for VP of growth and experience and so quickly for Good Eggs based in the Bay Area, currently Bay Area focused, but expanding all through California in 2020. We are an online grocery delivery service, but what we do is we work with 70% of all of our food is from local farms and local suppliers. It's 1% actually on average of any other grocery store.

The other thing about is we just have really high sourcing standards. Bananas are not grown in California. However, we have sourced them from a place that we know has the right labor and practices and the right way of essentially like farming and not cutting down any rainforests to do this. Very high standards across the board same with animals, meat, cheeses, and you got to get your whole basket and no, it sounds extraordinarily expensive but the cool part about it is we actually cut out a ton of the food waste and that's what actually keeps the prices pretty comparable. But I own basically the digital side of the house, the customer side. The customer experience and growth that means marketing product, BD, and our customer support teams.

[00:20:28] Matt: Man, seems like, between your love of food, your love of sustainability, this really hits the sweet spot for you.

[00:20:35] Anne: Definitely.

[00:20:36] Matt: I guess I wanted to ask you, maybe something that you'd be willing to share about what you love today from the result of this really varied career that you've had about life work and money?

[00:20:47] Anne: Yes, I will say, from work I feel so fortunate that none of the jobs that I just described did I ever feel like it was the punching in a timecard and kind of going to work. A lot of it, the intellectual challenges and just the ability to say, "Okay, here are the things that are immovable, but I'm sure I can find a lever, I can find something else to play around with." I would say that intellectual rigor and just like the ability to have so much fun creatively to build a business. I always say growth is kind of my sweet spot for when I'm working with companies, because there's a lot of R&D, and there's a lot of like, nope, that's not going to work but that's going to work and starting to then figure that out and see the signal pretty early so then you can start scaling it.

I feel really passionate about the work I get to do day in and day out. I'm always excited to show up to work and even more excited when there's something big that's launching, I get a lot of energy from that piece. Then I think from life and money as much as I just waxed and waned about how much I love my work but it doesn't even hold a candle to my wonderful daughter, my husband, my two crazy dogs that we have out here. One thing I love about California and my besides just the work environment that I get to be in, but it's also just an incredible place to get out on the weekends. It's beautiful. Not to rub this in, it's beautiful 60 degrees today here, we went to the beach. It's a great place to be and I feel really fortunate because I think that's something that just, you can kind of, it always reminds you when you have that natural beauty or that access to it to get out and take that more time.

Then I think from a money perspective, which I love that you're asking that and pushing because I've been also saying, we need to have these conversations, I've been really fortunate to work with companies and the one thing I will say is I get very upset when I meet anybody out here in Silicon Valley that's like, "Well, I'm a genius." It's like, "Well, no, you had a product-market fit and somebody invited you to work at this company and the falling economic conditions were all there."

I will always say that there's a 50% into being locked in the privilege that you get but the thing that I like and being able to do, the work that I do is it's helped us essentially be at a level where I don't have that earlier worrying about paying back of student loans back, right out of MBA. And then the other thing is being able to have taken this a fair amount on but actually being able to make sure that you are giving back and you're not just giving your $5 to your local NPR station like how do you actually really invest in what you think and take on that stewardship.

[00:23:28] Matt: Man. I just think it's neat to hear in pursuing these careers, you've been able to put your values into action in a variety of ways with your family and with your money and I appreciate you sharing about that. I also want to just touchback and say, yes, a part of what I hope to do with the podcast is remove some of the taboo around money discussions, it's such an integral part, and what you share highlights that anything that you want to do takes money, and so it's good to have some of it. If someone was looking at your life from the outside, it's gone really well and I think you would probably also say that it's gone really well but what's a challenge that would surprise someone who maybe didn't share a house with you?

[00:24:10] Anne: Yes, this is one of those that I think it can be seen as cliche but when you add in, on the personal side of life, kids, dogs, and you're doing a career, the thing that usually shrinks is your own personal time. I would say when you have the three buckets of life, work, and money, it is absolutely saying all right, I'm going to take a lot less on the personal side, and really let the expansion of essentially my daughter and all the time that I want to spend. That is always a challenge.

My husband also works really hard as well so it's these moments of not only us both being able to be home at the same time or he'll be traveling during the week which is a lot for me to be doing full-time job, picking up my daughter, keeping all the wheels moving and then he gets home and he's exhausted. So it's not only do we have to be ships passing in the night, but we also have to not want to be just falling asleep on the couch at that point too and actually spending quality time together.

What I love about tech and jumping in, yes, this also very much existing consulting too is the fanaticism. I think I enjoy the little bit of the craziness, mainly because it's that creative work, it's at building these. But there definitely is a dark side. I would say it's hard when you're in a predominantly male environment, I've been lucky enough to find certain pockets where I've had a female leader here or there where I have been able to like really feel mentored or a male leader that has said, "Hey, let me actually teach you this. Let me teach you to be more vocal to actually say, how do you actually make for that seat at the table, and then you continue to say, hey, this is what I really want to do."

I always think about essentially at Twitter, it was one of those great fortuitous things is they're like, "Yes, launch this." There wasn't quite a plan but it's like as things were spinning along, you came up with a good idea, you had to raise your hand say we should be doing this and I want to lead it as well and more often than not, there's nobody else around so be very sure you can lead that but that's very different from coming from consulting where you're like, "Never say anything on even keel to the client." There was a lot of how do you actually think about those norms and learning?

I will say that that was a huge-- I benefited from people taking me under their wing, but I also spent many a time trying to figure out what was that second language and how to how to use that. One thing I worry about or I talk about with money is my parents are aging and, unfortunately, my mother we had to put her in a memory care last year and helping out with that expense. I look at the boomer generation, I look at millennials and Gen X or wherever we fit into the in-between of those.

[00:26:50] Matt: We're the in-betweens.

[00:26:50] Anne: We're the in-betweens, it's fine. I feel like in the next decade is going to be a huge crisis of us trying to figure out how do we think about long term care for such a large generation and a generation that potentially has not saved as much wealth on that piece and then you compound it with others who how do you actually save for colleges if you're on retirement and continue to pay your mortgage? That is always a scary thing about that sandwich generation that I think, it's hitting me hard now. But I worry thinking about how are we going to do this in mass as a country?

[00:27:25] Matt: I think you sharing that from your personal experiences is pretty compelling. I think it will be a challenge for many families and that highlights both what's coming and the importance of planning.

[00:27:39] Anne: Yes.

[00:27:40] Matt: I don't know, I put this one in here a little tongue in cheek and but I wanted to ask you about your FuquaVision president career. I feel like for everyone out there who doesn't know, FuquaVision is a sketch comedy club at Fuqua and Anne produce some incredible videos there and I know you put a lot of time into that at the time. How did that fit into where media has ended up playing a role in your career, if at all?

[00:27:59] Anne: Oh, my gosh. I will say the sales conference at Twitter had a very intense parody video thing that each of the different teams and I destroyed it because when you're [inaudible 00:28:11] use my services. Instead of The Wolf of Wall Street. We did the mongoose of Market Street, which is where Twitter is on, it's very good. It came out.

I'm very proud of that and people were-- as I always had a very specific skillset on doing parody videos on like a two-minute mark. I love it because it's one of those-- I remember, second year, they made us do like a day of Second City improv where they brought it in, that's the ability to connect. The other thing too is as geeky as it was, we obsessed for hours over the fine-tuning of a joke, and how do you make it a little bit better and how do you make it more inclusive and make sure that it wasn't just a small inside joke that people could get it, that people could resonate on that? I think there's that nuance, that's positioning work, and so a lot of that fun was actually some of the best like being able to be in a workroom and talk about how do you bring something to life. It's not a shocker that most of the few division as presidents are all in marketing doing amazing things.

[00:29:13] Matt: Sure.

[00:29:13] Anne: The other thing too is it just, it taught me to just go out there and be myself from day one. I feel like no holds barred and that is how I went into the workforce having that a sense of fearlessness definitely helped me early on.

[00:29:26] Matt: I think it's neat. I would do more with FuquaVision if I could go back.

[00:29:29] Anne: Yes.

[00:29:30] Matt: I will say this, Louise and I took an improv class together this last spring and that was super fun. I have to put that out there. It's something we enjoyed.

[00:29:38] Anne: That's amazing.

[00:29:39] Matt: Yes, it was good. I'm a planner, and this is a show about planning. If somebody wanted to build a career like yours, you've shared some things that are serendipitous like I wrote down three things that I've always seen in my life and you've exemplified is just ask, just try, just go. I thought, just ask and you got into Duke, just try and someone asked you to do lead-generation work and just go if Twitter comes and knocks on your door, but how would you counsel someone to plan for a career like yours?

[00:30:07] Anne: Well, there's this funny thing that happens still to this day and I'm like, guys, seriously, like there's a much bigger, more robust pipeline, but I will get a, a very overeager second-year Fuqua MBA that will be like, "I just got an offer from L.E.K and I saw you went there, but I saw you ended up at like all these other things. Can you tell me if I should take that job?" My big piece of advice is always what is your angle? What do you want to do after that? Because it's really hard. There are very few, it is not the norm anymore to take a job and get a gold watch after 50 years and getting to retire from there. Particularly here in Silicon valley, if you're at a company for more than two years, people are like, oh wow, you're one the old ones you've been because the average length is usually a year.

There's a lot of career hopping, but it's usually because there are these opportunities. I felt a little, a little nervous about that when I first came, in fact, leaving Trulia for Twitter, I was there for just a year and I was completely freaking out because I was like, "That's not what you do. The career center or like at Duke will come back and take away my MBA for being so irresponsible." That's what you do is like you seize the opportunity because it's not always going to fall on your lap. Then also, I don't know. The other thing when they call, as I say as figuring out where you want to aim towards but don't be laser set on it because there's going to be a lot of other stuff that you'll be able to pick up along the way.

Then I had this incredible mentor. He was my boss at Twitter. He's the guy who wrote the Radical Candor book. He had this thing. This is his advice from when Sheryl Sandberg was his boss. As you need to have a wild vision and an 18-month plan. Instead of saying what are you going to be when you grow up, he would make everybody less. This was of his directs would be what are the five things you want to be? You had to pick between three and five because there's that one thing that you want to be, you're going to get that analysis paralysis. We would go through, we talk about all of those and then you find the commonality. If I was like CMO, he'd be like, "Well of what type of company?" You'd be like, "Well honestly I'd want it to be something a little bit more mission-driven." It couldn't just be any company.

It's like, "Well, what are you selling there?" You'd have to start to paint this robust picture. One of them usually was, have to be the complete path not taken. I always said, mayor of San Francisco, I'd love to be mayor of San Francisco. I think that's the right level of politics I'd be willing to engage in. The interesting part about that was why mayor? It's an executive. It's not the legislative it's the idea of running the whole business. You take all those, you cobbled together and then you look at your skill set and say, okay, well let's see, 18-month plan of the one thing that you don't have that actually fills out to any of these. Is it more deepening in finance? Is it more actually saying you ran the PNL yourself, what are all those different pieces? Then go for that because you can't do everything at once. I think that is the biggest thing that I've learned is if you over-planned, you're just going to disappoint yourself, but have a strategic plan and the tactics to be honestly, it should be a little bit more passive and don't get lazy about it.

[00:33:03] Matt: No great advice. I appreciate you saying it. A big theme of this show is learning from the experience of others. If there was one piece of advice you wish you'd heard earlier or wish you'd put into practice earlier, what would that be?

[00:33:17] Anne: I will say I heard this advice. I was actually very lucky. Madeline Albright came to Twitter and did a-- with us 30 women [unintelligible 00:33:25].

[00:33:25] Matt: I remember you telling me that time.

[00:33:25] Anne: It was incredible because we were asking her advice and she is such an incredible and accomplished woman. Just being in a room with her, it's like a whole new level of just respect and understanding. Her main advice she kept telling us is you can't do everything at the same time because you're either going to burn yourself out or you're going to do it in a mediocre sense. She got her PhD, she was a stay-at-home mom for a while. She was also the first female Secretary of State. She was like, you have so many chapters. If you try to think overwhelming about it, you're going to trip yourself up so pick a goal, work on it. Then it's okay to leave space for the other places.

I got to meet her when I was pregnant with my daughter. It was just one of those amazing things where you're like, all right, this actually helps me figure out how do you get that work-life balance a little bit more and say there are short-term and long-term goals and it's okay to say, I'm going to focus in on this, but I'm actually going to then have the reflects of that and move on the other side of the house of a little bit more, take some time off with my daughter.

[00:34:36] Matt: I think that's awesome. I liked that way of saying it you have so many chapters. I think it was Peter Drucker who said, "People, tend to overestimate what they can do in a day and underestimate what they can do in a year."

[00:34:46] Anne: Absolutely.

[00:34:47] Matt: You can underestimate what you can do in five years or a decade as well. Then pair that with what you said earlier about not getting lazy. That's a recipe for some balance that still gets a lot done. I wanted to ask you, Anne, are you reading anything interesting right now or any books that have been real meaningful to you?

[00:35:05] Anne: I would say the last thing I read, I put down, which I would just say everybody should read was super pumped. It's the rise and fall of Uber or the fight for Uber by Mike Isaac, who is one, one of the best Twitter followers like follows that you could have out. He is an absolute, incredible tech reporter out here in the Bay Area and really good dog photos. He has an amazing Bernese mountain dog. The book is gripping and he did so much of the reporting. He broke a lot of the 2017 tumultuous around Uber, but it's already been optioned by Showtime, the people who make Billions, are going to turn it into a show. It is such a compelling read. I think it also captures a certain time in the atmosphere out here.

Before just being like, "Oh, what is tech doing?" It actually shows a lot of the questions and the questions around and what does it mean to take on more money? I don't know. I love it. I actually think it's a really good one of those, like, this will be a good 2010s book when you go to reflect back. Then, Tender at the Bone, which is Ruth Reichl's book about her mother. I just re-read that in the fall. I'd read it years ago. I just still think I'm in a place of what is legacy and what are the things that you do with your career as you reflect back on like your parents and thinking about your childhood. Her mother actually was horrible at cooking. She would scrape mold off and be like, it's still good and cook these spoiled things in the fridge. She's one of the most prevalent food critics of our time right now.

[00:36:41] Matt: She knows what she does what she does not like.

[00:36:42] Anne: Yes, so it's really interesting for her through-line on what her mother gave her, what her mother challenged her on and her reflecting back on how it actually went to her, making some career paths in her career. It's funny to read it like 10 years later after I read it the first time. I love that book.

[00:36:57] Matt: Man, I really appreciate you sharing those because I was not clued into either of them and I love getting new books. Well, and is there anything I didn't ask that you'd like to share?

[00:37:08] Anne: I don't know. I think the biggest thing on-- first off, this is a really awesome podcast and way to start thinking about how do you start these conversations? Marketplace is doing a series called, Well, This is Awkward and it's similar talking about money right now. I think the more places the better should be talking about this. I think the one thing as you said, like just asking for advice, being completely frank, that's the one thing that has helped me cut through so much either like an anxiety or just like not knowing what to do, just coming from that place of humbleness of saying like, I don't know what I don't know, has been really important for me. I think that goes for all aspects of your life. Continue challenging people to talk about that because I think the more we do that, honestly, we just save so much nervous energy we don't need to have out there.

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[00:38:05] Matt: Now here's the July 2nd, 2020 interview with Anne. It happened when I realized she changed jobs between the time of our first interview and that shows publication. In our conversation in January you said that if you get too long-tenured in a job in Silicon Valley, like approaching two years, people start to look at you funny. I wanted to ask, is that what drove your change? If you could tell us your story.

[00:38:31] Anne: First off, you can stay in a role for more than two years in Silicon Valley. It's just the joke that we are an ADD culture, but I will say a big change that happened last six months is quite frankly, we had scaling issues that was going on at Good Eggs. Between that and knowing that we needed to preserve our burn, we decided to do some layoffs. Then I looked to personally in my life and said, listen, there was actually a lot going on. How do you homeschool a child suddenly when you're put into that role? As well as I mentioned a lot that was going on with my mother across the country and trying to take care of her, and took this moment to say I built an amazing team.

Some of the best advice I ever got was from one of my mentors at Twitter, Russ Laraway. He always said to work yourself out of a job. I had built this team. There's some people who worked with me for over 10 years now, multiple startup companies they've jumped and it's amazing to watch them become these leaders. It was actually a pretty easy decision to say if you guys are not in a big building section of the business right now, and it's more about taking the demand in that they have and figuring out the scaling, I think it's a perfect time for me to step down. It's been great because I've been able to balance some really good time with my family, as well as I think, like take a nice pause. 2020 throws a lot at you. I actually feel like it's a nice moment to actually be able to have a little bit more of that space and that time.

[00:39:55] Matt: When you said that to me on the cell phone before we got on here, I thought that was such an important thing to be able to share both how the planning that you put in place prior to this set you up for the situation, and then also how you had taken that advice to heart to build the team that could manage without you, and then because of that you were able to step away and do these other things. I wanted to ask, basically, as you engineered your own layoff, how did you bring that about?

[00:40:22] Anne: I mean, I think really being able to think about who were the pieces that were strongest for all of my different team members that I knew that they could just step in, but also making sure that I was giving some growth opportunities as well. I have this phenomenal woman, Jane, who I mentioned, has worked with me for four different companies now, and to be honest, she is such a strong people manager, even giving her more of the direct reports.

Kind of expanding her smaller team into a bigger team, because I knew she could do that and it's been fun, because, when I first hired her, she was an IC. She'd only work with an IC, but you could kind of see that management skill and it was making sure not to overwhelm but to pass additional pieces of the work off to people who I knew would actually be really excited about the growth opportunity. One thing I've always done in management is ask, what's the next thing you want on your resume? And some people are going to be very precise about it that went like, I grew the business from X to Y, and some want experience, some want tactics, but like knowing that and like, it's a great way, one, to manage while you're there, but also it helps kind of keep the conversation more about their career growth, and not just like what we need to get done day-to-day. That was kind of the nice thing is I had that layoff there and then the other thing, from personally, like, I will say, like, how do I approach it just as a human?

That's the other fun thing in Silicon Valley, I have had people who work with me more than one company, I've had people, that come in and out, they reached out and said, "Hey, whenever you have this role, if you ever are bringing, performance marketing in house, let me know." That's the fun part is like, you've done a really good job, because I had a bunch of people who worked from Twitter or from IFTTT, or others that had reached out that there's other ways to build and kind of taking off this summer has been really nice, too, because it lets you think about, it lets you go back into the dreaming part of like, what do I want to build? I think it's been also really nice to start to define like, what were the things that you really like best about your job. I've been trying to say like, this is very specifically what I'm looking for, and be very, very intentional about kind of my next step.

[00:42:24] Matt: I think that's terrific. Now I wanted to ask, and you can take this question any way you want about any part of your family's plans but what role to the fact that you're a two professional earner household play in your thought process around leaving Good Eggs or what other types of planning have you done that made this transition easy to swallow?

[00:42:44] Anne: Now, I will be very honest, the fact that we are two in our household, it was extremely liberating, because it let me make the choice that I really want to do. I will also say that we are the conservative savers' planners. We also kind of have that in the background as well. Being able to have severance plus the savings that we had, I think the other interesting thing was just sitting down, and having a real discussion around COVID. Quite frankly, we are one of those couples, that is spending a lot less. We’re not going out to dinner, we are not taking our big vacation this year, because we're not going to fly across the country or rent a house. We're keeping it a lot more local, which when you look at those things, your actual monthly spending goes down significantly.

It was nice people to have that breathing room. there was actually a time pre-Sean and I getting married, where he had to transition into the consulting firm that is that he's at now and he took several months off and it was great as a double earner, that we could be able to balance that for each other. I think you see a lot of grace in that you have that partner and you guys can have those more frank conversations and know that you're supporting each other.

[00:43:53] Matt: I think that's one that's interesting to me. Because on the one hand, there are definitely inherent challenges that come with managing to professional careers side by side, I think that can be really tough and put pressure on a family. On the other hand, when you're able to do it successfully like you and Sean have done. It also creates this diversification of your income streams that's nice when one of you wants to do something different. I think that's terrific. What advice do you have for other people who may be looking to make a transition from their current deal, either to prepare for that or to make it happen?

[00:44:27] Anne: If you're thinking about that, quite frankly, you've come to a point where you don't want something currently in your life, something isn't working but the big trap the thought trap that you don't want to get into is constantly obsessing of why it doesn't work. It's getting yourself to a positive place of saying, "Okay, what do I want?" You actually have a lot more of that kind of proactive idea of saying, "Hey, there is a simple way to change it." Because it's easy to say I don't want this but, but, but, but or, I don't want this I never want to do X or Y again.

For me, it was a couple of things. One, I will also say another like kind of piece of advice I've gotten to, like, hold very near and dear was, this is ridiculous but when we were at Twitter, we had Madeleine Albright come in, and she was doing kind of a live chat but she did a small group of kind of talking to women Twitter beforehand and, somebody was asking her, like, how do you do it, and you plan this career, and you raised all these children to have a PhD and our Secretary of State. She's like, "Honey, there was a whole different like time horizon there, and you just squished it all into one spot." It was life-changing. She was like, go for what you want, but figure out what the plan is in the path, or else you're going to drive yourself crazy.

For me, I thought it was actually really important, one, to take some space to get into that positive, like, what do I really want? How do I want to distill this together? Two, the elephant in the room in this COVID world is children and daycare, school, all of that being on pause is that suddenly it throws a double working household into complete chaos. I was feeling really bad that my daughter was on a Zoom call, and I jumped on a Zoom call, in fact, fun fact, she cut her hair, I'm acting out because I wasn't paying attention while I was on a Zoom call. I've learned how to become a stylist in this time to clean that up, but I think the broader thing is saying, "You know what, I actually want to take this moment but I'm not just taking this moment, because these are the roadblocks that are in my way, I'm taking this moment to say, one, enjoy some time with your children, and like be okay with the fact that things aren't working right now but then be really intentional with what I want out of a job next."

What do I want out of the people I'm working with next? I think the other big thing is if you're thinking about that transition, yes, there's a lot of I want to work for X or Y with this product, or, this type of business goal but to be honest, I spend a lot of time and then thinking about who are the people that I want to be working with, that can kind of have that understanding and grace? The people who I talked to that are totally fine having their kid walk in on a Zoom call verses the ones that are just pretending like absolutely nothing is happening.

It's a really, really great rush app, but of how somebody is going to actually work with you. I would say it's the planning forward and being okay, that if you're not just going to come up with the right thing, right away in 15 minutes, but it's going to be fleshed out over a couple of days, weeks, months, whatever you need through there. It's actually really exciting once you come to a distillation of what you really want.

[00:47:27] Matt: Well, that's terrific. You've talked a little bit about what you've been doing kind of from a family standpoint, but you've also added I think, a board seat during this time, is there anything else you'd like to share about what you're up to at the moment.

[00:47:38] Anne: I think there's two really interesting things and you can find this as well, I just went back to my network and, I said, Hey, I'm actually taking the summer off. I want to be here and be present for my child, I don't want to just try to scrap together a bunch of things. I'm doing a job search, but it's passive until essentially, the alleged school year starts again and then we'll figure out other ways to make this work. But it was great because there's a couple of things that happened. One, there's a little bit of out of the blue, I'll be very honest, for somebody just ping me and said, "Hey, I know this amazing woman, she's junior, and she needs a mentor, she just got a senior marketing role help mentor her." This was a mentor of mine, which I was going to pay forward no matter what, which then turned into a consulting engagement.

Then two, just reaching out and kind of like having discussions actually using the time. I had a friend who I've known for many years, actually, get her startup business to a really good place and she's been using COVID to kind of really be able to lock in funding and really be able to scale and she came and said, "Listen, you have the right experience that like I would love for you to be like an independent board member and help me really figure this out." It's also been fun too to be using that other part of my mind and that kind of strategic piece on it isn't all just kind of like what job search or just children, it's actually taking on the projects that I find really interesting and also getting to work with people who I really love that suddenly, it's time have these opportunities. I'll be very honest, instead of saying, like, "Oh, I'm just going to kind of keep the LinkedIn behind or not talk about as I make my job." It's been really fun to just catch up and have real-life conversations with my network and it's amazing the opportunities that just kind of fall into your lap.

[00:49:11] Matt: It's the joy of an integrated life, it may become addictive Anne, you may not be able to go back to the 50-hour week. I guess you'll have to see, I'm sure you'll get it figured out. All right, well, I feel like you've talked about what you're doing now, you've talked some about what you're looking for. Is there anything else that you'd like to share with us today?

[00:49:28] Anne: I think the big thing is I try to not be Pollyanna about it but take like where we are in this world. There's many things we realize weren't working when you kind of throw a pandemic on top of like the macro culture that we're looking at but it's a really great moment if something is still really not working, not just be frustrated about it but to actually say like, "Hey, what are the ways that I actually want to change?" I think we're all mourning that we have to change. Everything is changing, but getting over that next step of kind of like, "Oh, it can't be the way it was." I'm trying to take it as an opportunity of painting, what I want. What do I want it to be? I don't know, there's a hopefulness about that. Also, it's not just magically like, we're going to be through this really quickly, in my opinion, but I do think it's been a lot of fun to, I don't know, just take this year to actually not just do the day-to-day. We always joke like, what is time anymore when you're in your house all day long but there's been a lot of actually great thinking versus just like the weeks that you put down, and all the meetings and stuff that you're able to get done. I'm viewing that as a really unique benefit of this year.

[00:50:39] Matt: 2020, has got a big old reset button on it for a lot of people.

[00:50:42] Anne: Yes.

[00:50:43] Matt: It's been really interesting times, and we all look forward to the future but I really appreciate you sharing how you are using the time right now. Thanks for agreeing to come back on and talk about a big transition.

[00:50:54] Anne: Oh, always. Love to chat with you, Matt.

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[00:50:59] Matt: Anne cites the importance of her personal board of directors. If you can't identify who the two to seven people are that make up your personal Board of Directors, this item needs your immediate attention. Anne is generous to put my efforts alongside Gretchen Rubin. Where I think I can agree with this idea is that Gretchen and I are both sharing our ideas to make our living and to make the world a little bit better. Takeaways from earlier conversations with Anne include her recommendation to show up and do the work, to not only propose ideas but to lead the implementation effort. Anne points out that you can't do everything at the same time but you can fit a lot of accomplishment into a lifetime if you keep putting one foot in front of the other. Next week's show features two great interviews. A brand new show with entrepreneur Steven Valencsin of Growers. He and I talk agriculture, technology, and life alongside selling a business and then staying on as manager. Then on Friday, I bring back one of the most popular Shows of All Time, an interview with Shane Dikolli, professor of accounting at the University of Virginia's Darden School of Business. Thank you for sharing your time with me today. Until next time, this is Matt Miner reminding you to make a financial plan that works as hard as you do.

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[00:52:20] Female Speaker: Matt Miner is a fee-only fiduciary financial advisor and founder and CEO of Minor Wealth Management, a North Carolina registered investment advisor where Matt provides personalized unconflicted advice to clients for a fee. He's also my dad, so please be nice when you talk to him. Matt is a certified financial planner professional and holds a series 65 securities license. He earned his bachelor's degree in finance from Arizona State University and his MBA from Duke University's Fuqua School of Business.

Work Pants Finances, is Matt's financial media business where he talks about work entrepreneurship, kids and money, taxes, investing, and other personal finance topics. Workpantsfinance.com exists to share wisdom and provide general financial information. It is not financial tax or legal advice. You are an individual and probably need personal advice for your specific situation. You should consider building relationships with helpful caring and competent professionals who understand your unique context and can provide advice that is tailored to your needs.

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Matthew Miner