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This season, we talked to 12 entrepreneurs—11 of which happened to be women in tech—and there’s one question I asked of every Proust participant that stood above all else (at least for this writer): What’s your favorite book?

In return, I got the names of comic strips, and self help books, and fiction books that have inspired a wave of tech professionals in some way. Long story short, if you’re new to tech and need inspiration and knowledge, these books may contain the lessons you need.��

1. , By John Steinbeck (As recommended by Paola Santana, the founder of Social Glass, a software startup to help government organizations communicate better.)��
2. by Paul Coelho and by Keith Ferrazzi and Tahl Raz (As recommended by Lolita Taub, the chief of staff at Catalyte and a previous principal at Backstage Capital.)
3. by Dale Carnegie (As recommended by Kaan Gunay, the CEO and founder of Firefly, a car advertisement startup.)
4. by Leo Tolstoy and by Gretchen Carlson (As recommended by Elizabeth Ashford, the senior director of communications at Eaze, a cannabis delivery startup.)
5. by Charles Duhigg. (As recommended by Erin Bury, the CEO of Willful, a Toronto startup that helps people make wills online without seeing a lawyer.)
6. by Frank Wilczek (As recommended by Alex Marshall, who works on special projects with First Round Capital.)
7. by Tim Ferris. (As recommended by Rachel Murray, the co-founder of She+ Geeks Out.)
8. and by Trevor Noah (As recommended by Jody Rose, the president of the New England Venture Capital Association.)
9. by Chris Voss. (As recommended by Andrea Walne, a partner at Manhattan Venture Partners.)
10. by Nassim Nicholas Taleb. (As recommended by Maia Bittner, co-founder of Chime-owned Pinch.)
11. by Amir Levine and Rachel Heller. (As recommended by Sarah Kunst, the managing director at Cleo Capital.)
12. by Quino. (As recommended by Natalia Oberti Noguera, the CEO and founder of Pipeline Angels.)

Bottom line: this would be an awesome place to start if you’re interested in starting a book club of your own, or just want a masterclass on what it takes to raise your hand as a tech professional. I’m going to read some myself, too, starting with Kunst-recommended Attached. Let me know what reads end up being your favorites.��

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In this Proust Goes Tech, Oberti Noguera tells us about the book that nurtured the rebel in her, her favorite tweets, and what a human rights technologist once said about her.

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The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

I’m a huge believer in the power of being a multi-hyphenate. I did double major in Economics & Comparative Literature in college. So there’s a chance that I may soon be doing something around helping create a more accessible world beyond what I’m already doing at Pipeline Angels and Pitch Makeover.

Your main fault?

Puns.

Your idea of misery?

Trying to convince people who dehumanize a community of that community’s humanity.��

Additionally, as JP Brammer’s says, “I’m sick of ‘turn the other cheek’ rhetoric from people who aren’t being struck.”��

What do you appreciate the most in your friends?

When I read Dr. Thema’s , “I hope you find someone who speaks your language so you don’t have to spend a lifetime translating your spirit,” it greatly resonated, and I’m grateful to have a partner and friends with whom I share languages. I’m intentionally using the plural, as I believe it’s possible to learn and know more than one language in relationship—platonic and non-platonic.

Your chief characteristic?

I asked my friend , a human rights technologist, and she said, “When I describe you to other people I first say that you are someone who works hard to live their values and next mention what a great champion you are to others.”

It meant a lot to be reflected back so closely and clearly to who and what I strive to be. It is a daily practice.��

Your most impactful book?

A book that influenced me as a kid and nurtured the rebel in me was the comic strip by Quino. Mafalda, a six-year-old Latina, is told by her mom to not open the door to anyone before heading out of the apartment and, as her mom is waiting for the elevator, Mafalda peeks out into the hallway, and asks, “But what if it’s happiness?”��

What do you look for in a tweet?��

Big thoughts made into one-liners. Something that makes me think and do a double-take. Like when Imani Barbarin : “Disability isn’t on me to overcome it’s on you to include.” Or Keah Brown’s , “What some people need and don’t have is people who will call you in before you need to be called out.”

Also Dominique Derbigny’s :��“If you’re talking about race and gender equity without talking about white supremacy and patriarchy…what are you really doing?”

What defines success?

Impact.

When is confidence lost?

I’m more interested in helping create spaces where women, non-binary people, and men of color get a chance to gain confidence in a world that automatically grants confidence to white men.

Which buzzword is exhausted?

“We couldn’t find any women, non-binary people, or men of color to feature.”

What impact do you want to leave behind?

Getting systems to lean in. Scaling my saying, “When the most marginalized are leading, that’s when inclusion happens.”��

What’s the biggest problem tech is failing to solve?

White supremacy.

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She would buy video games from garage sales, then auction those same discs off on eBay for a profit.

“I was like, literally, strangers are sending me money in the mail,” she told Crunchbase News over the phone. She loved the concept of mail so much that she would’ve made “a career out of it.” Fast forward two decades and a move to the Bay area, Bittner resorted to founding her own company: .

Pinch helps apartment renters that pay their rent on time boost their credit score, and it was acquired by Chime in 2018.�� She’s currently still working with Chime and invests as a Sequoia Scout.

In this Proust Goes Tech, we learn about Bittner’s favorite neighborhood in San Francisco, the lunatic behind her favorite novel, and what she wishes she knew in her 20s.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

I would be a tour guide. I love giving walking tours of different neighborhoods in San Francisco or New York; I feel so alive. I think half my time my friends are indulging me, and the other half�� of the time they are actually interested.

I love Western Addition in San Francisco. It has a mixed energy with all this different industry. The neighborhood is known for sushi and jazz music, and I love the physicality of its history: the history is a little yucky and sometimes not sugar-coated.

Your main fault?

I’m not very good at working with other people at a peer level. I’m good at reporting to people above me and working with people below me. While collaborating on a peer level, I tend to discount my own opinions and feel insecure in what I think. It makes my partnerships not as strong, and I think it comes across in work, very obviously in romantic relationships, and in friendships. I think there’s this balance between preserving myself and what I want and not wanting to disappoint other people.

Your idea of misery?

When I can’t make progress on a problem to move forward. Any time when I don’t know the next step, I fall into despair.

What do you appreciate the most in your friends?

I know this is going to sound snotty, but there’s a lot of people really look up to me, and I’m not into that. I’m so human. It’s my friends who push that have been the most valuable to me.

I have one friend that always asks, “Can I ask you a provocative question?” And I’m always like, yes. And then it’s always an interesting question. And I’m like shit. Yes. Yes. Please send all provocative questions. Always.

Your chief characteristic?

Curiosity. I’m really endlessly, and so certainly, curious. I always kind of want to pick apart stuff and unravel it.

What’s a skill you wish you possessed?

I wish I was better at connecting with people. I feel like that is not a strong suit of mine. But Twitter has helped me with that, weirdly.

My is very vulnerable and in a pretty performative way. So there’s energy, and it’s entertaining. But then I’ll get coffee with someone I meet from Twitter, and they’ll kind of ask for me to tell them a funny joke. Or an off-the-cuff interesting metaphor. But I think really slowly. So I tell them, most of the time, I am quiet or reading or something.

The quality you most desire in a tweet?

I love Twitter because it feels like a non-stop new idea dopamine rush. Like, is this new? Is it plausible and interesting? I feel like there’s an infinite number of new ideas and new ways of seeing the world.

Your most impactful book?

“” by Nassim Nicholas Taleb. He’s a lunatic. He kind of barely pulled it together to write this book. It is about our propensity to try and predict.

What defines success?

Success, and for what I’m optimizing for at every turn, is the freedom and ability to work on things that I’m going to work on.

For, like, all of my 20s I basically didn’t think about impact as a form of success.�� I was, you know, proud of the work that I was doing in the way that I was going about it. I’m 31 now, and wish I thought about that sooner.

When is confidence lost?

I would say confidence is lost with inconsistency. Or it’s when confidence in leaders and organization goes back and forth a bunch and nothing makes sense. Sometimes, it’s better to know the path you’re on and stay on the path versus switching between different paths.

Which buzzword is exhausted?

I like buzzwords!

I think when somebody says they have an AI startup, what they’re trying to say is, “I’m creating something really valuable here; it is really important to us. And I want to be associated with this class of extremely data-driven startups who are investing in this infrastructure and focusing on it from day one.”

What virtues do others have that you don’t?

I’m a little gossipy; I wish I was more firm. I can’t imagine saying, “I can’t tell you that.” I’ll always answer questions. I would be the easiest person to interrogate in the world.

What impact do you want to leave behind?

I really like entrepreneurship and seeing people carve their own way into the world. I would love to encourage more people to do that.

What is one problem tech is failing to solve?

I think there’s a bunch of problems, and tech shouldn’t solve all of them. But I think one of the things it affects, but it’s kind of ignored, is that tech has an opportunity for a really big impact on culture.

But the cultural impact of tech people has been hoodies and ugly shoes, you know, and it could have been empowering employees of an organization or bringing inclusion.

But tech is not leveraging all that. It’s just like, oh, yeah, hoodies are cool. Like, that’s what’s done with its power.

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Walne is the newest partner at Manhattan Venture Partners, coming from a background as a founder and operator in the startup world. She has a soft spot for supply chain, and doesn’t mind when her friends laugh at that nerdy tidbit.

For this Proust Goes Tech, we catch up with Walne and learn about why she doesn’t mind ignoring Slack sometimes, how slow walkers make her miserable, and which book is in her top three favorite business books of all time.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

If I had the guarantee of financial freedom I’d be in the winemaking and distribution business. While there’s implied romanticism of working in the wine industry, at its core it’s cultivation and farming and operates on slim margins. Beyond growing a vineyard, I’d love to manage a tasting room and build out the distribution and marketing channels for the various wine labels. I’m the type of person who embraces meeting new people constantly, so the revolving door of foot traffic in a tasting room is the type of environment I think I’d thrive in.

Your main fault?

My team would tell you that it’s my tendency to skip meals during the work week. Aside from that, I struggle to “turn off” in periods of perceived downtime. I’m working through ways to mitigate this. I’ve started leaving my phone behind when spending time out with my family in order to focus on being in the moment. Our time is fleeting and I know that as I get older the memories I build now won’t be built around my Slack message response time.

Your idea of misery?

A narrow sidewalk in which I’m stuck behind a pack of slow walkers. I walk like a New Yorker – with a purpose. I don’t understand how people operate otherwise.

What do you appreciate the most in your friends?

Trust, honesty, and an ability to give me a painful amount of constructive criticism, whether it’s solicited or not. Throughout all walks of life I’m grateful to say I’ve built varying types of friendships that I cherish immensely. My friends and network span across diverse backgrounds, and I’m humbled by those that lead a life that is polar opposite to mine.

Your chief characteristic?

Fierce loyalty to both people and a mission. I don’t do anything in life unless I would stand behind it and be accountable. I put an emphasis on this as I evaluate and build teams both from an investing and recruiting perspective. I also consider myself to be incredibly pragmatic and don’t take things personally, which I’ve found is off-putting to those who lack confidence in themselves.

What skill do you wish you possessed?

I really wish I could consider myself fearless when it came to physical activities. I have a low risk tolerance when it comes to anything I think can land me in the hospital.

Your most impactful book?

Never Split the Difference by Chris Voss. This is hands down one of the top three most important business books someone in a business/startup role should read.

What defines success?

The ability to deliver and have personal accountability for goals you set for yourself and others. I evaluate success similar to how I think about freedom, which is having the ability to choose how you want to spend your time.

When is confidence lost?

When there’s been rapport established and the counter party still can’t (or won’t) tell you what they really want or need.

Which buzzword is exhausted?

Pre-seed. I believe that the concept of pre-seed is too loosely defined and carries a connotation that a fundraising event doesn’t merit the label of a round because it was likely relatively small.

What virtues do others have that you don’t?

Compassion to the extent of giving everyone the benefit of the doubt. I tend to take a conservative approach to trust.

What impact do you want to leave behind?

I want others to remember me as someone who made them feel incredibly comfortable showing their own strength and doing it with conviction. I think everyone has a story to tell and a lesson to share, and many aren’t given an outlet to do so. I also want to continue empowering people to feel as though they can take an untraditional path to success. The stigma of going to the best schools and landing a top tier job right away is slowly fading, and it can’t happen fast enough.

What’s the biggest problem tech is failing to solve?

It’s disheartening to see how antiquated the intake and patient care systems within the medical field still are. There is so much left to build to enable healthcare technicians to do their jobs effectively and swiftly, especially in emergency environments.

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Beyond massages and a nice dinner or two, the group focuses on accomplishing one activity during the getaway: establish a goal for the year.

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This year, Rose made her goal to “be bold.” She says this focus makes her a better mother, daughter, and leader. Day in day out, Rose is busy working as the president of the (NEVCA). She has been with the team for 12 years.

In this Proust Goes Tech, Rose riffs about imposter syndrome, unicorns, and why she admires .

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

If I could dream big, high in the sky, I would be a singer and entertainer. I’d be something on the creative side. I have a musical home and background in my family.

Your main fault?

“Main” is a good disclaimer, because I have many. I’m my hardest critic to a fault, which sometimes inhibits me or prevents me from taking a bold, daring step. I struggle with confidence and questioning myself.

For example, one of the programs we launched at NEVCA, now going into its fourth year, focused on the challenge of diversity particularly within latinos and tech.

I’m not an expert at diversity and inclusion, so I felt really nervous and almost didn’t launch the program. I got imposter syndrome, and I had just gotten the role at NEVCA.

But I believe that diversity in tech is not just a Silicon Valley issue, it’s a Boston issue. NEVCA should be at the helm.

With the help of my co-founder I decided to take the leap. It was a seven-month ideation and conversation process before we decided to pursue it.

Your idea of misery?

Regretting not taking a leap. Misery is looking back and wishing I would have done something and didn’t because of fear. Basically letting fear drive my decisions.

What do you appreciate the most in your friends?

Trust, accountability, and transparency. I have a big friend community, but I have a couple friends that know what’s happening and that hold me accountable. They are honest with me, and for me, that is the most important thing in a relationship. I didn’t realize how important it was to me until the last 8 years of my life.

Your chief characteristic?

I am a motivator. I am trustworthy. And I am someone, who if I believe passionately about a vision or an idea, gets the train moving. I’m visionary.

What skill do you wish you possessed?

I wish I was more organized; I wish I had a strong operational foundation.

I rely on my notebook and my calendar, but I haven’t found any task masters or any kind of products to stay organized. So let me know if you do.

Your most impactful book?

I would say . My faith is really important to me. It’s my script and drives everything I do. I would also say a book that I have been completely blown away by and inspired by is “” by Trevor Noah.��If you’re going to read it, do it through his audiobook.

What defines success?

It’s my family being cared for. Are they happy? Are they at peace? And have I contributed to that and the broader community?

When is confidence lost?

If I’m being really honest, it’s lost if I feel like I’ve let my team down.

Which buzzword is exhausted?

Unicorn. I think sometimes it places so much value on having companies or investing in companies that are going to be the next unicorn, versus investing in companies or building companies that are impacting the industry in which it is in. What about companies that bring in a ton of returns for investors and are making an impact? I wish we would focus less on unicorn creation and more on that.

What virtues do others have that you don’t?

I would say consistently working out everyday. I would also say balance. I find work-life balance to be an elusive concept. At any given point, I’m failing as a mom, as a wife, or as a leader. It is impossible to have so many balls you’re juggling and keep them all in the air, and I think we need to accept that.

What impact do you want to leave behind?

I want to know that I made an impact in people’s lives. Whether it was pointing them to opportunities that they weren’t thinking about or providing entrepreneurs with opportunities that were hard for them to achieve. Also, I want to make a difference in the investor community.

What’s the biggest problem tech is failing to solve?

A macro issue it is still failing to solve goes back to equity and inclusion, and making sure we are creating spaces and technologies where women and people of color are seen as “in the know.” Again, it’s not just about unicorns.

To me, equality is the day that appoints a female CEO, and the headline of the Boston Globe of the New York Times isn’t that they appointed a female CEO, but that they’ve appointed a new CEO and here’s her background. I’m looking forward to that day.

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She had just thrown an event for , the Boston-based organization she co-founded with . She+ Geeks Out was created to empower more women in tech, and does so through national workshops, seminars, and happy hours.

“A woman came up to me and said ‘I just want to thank you for doing this event, I almost didn’t come because I’ve had some trauma recently and I just didn’t feel like I could do this,'” Murray said. Even though years have passed since, the moment reminded Murray that there is movement in getting women to feel more empowered within the workplace.

In this Proust Goes Tech, we’ll find out about Murray’s recent decision to ditch Boston for San Diego, her cheat to running long distance, and her two business ideas beyond She+ Geeks Out.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

Other than having lunch? I would probably still be an entrepreneur and run a business. I’ve always had a lot of ideas. It would probably be something else I was passionate about. The last business I had was about helping people find non-toxic personal care products, because that was really hard to find. It was my own company, and I had the idea back in 2012. I also had another idea where people could come in and do photo shoots in beautiful spaces for the day.

Your main fault?

My biggest issue is impatience. It’s something I work on frequently. I try to slow down a little bit, and it’s one of the reasons I’m moving. I think Southern California is a slower pace and I want something to help me recognize that it’s okay to slow down and not to expect everything immediately.

I use the Calm app because I do my best to meditate. The other thing I do, which is probably even more helpful than meditating, is running. I’ve started to do longer runs, and I did my first half marathon in May.

One trainer I keep looking at, she talks about how the limits when we’re running is not so much about physical discomfort but about impatience and wanting it to be done. That stuck with me.

The quality you most desire in a tweet?

I’m not a big Twitter person; I’m more of an Instagram person myself. But when I am on Twitter, I’m a big Giphy fan.

Your idea of misery?

Probably doing the same thing every day for the rest of my life without seeing any possibility for change. That is the worst. I definitely need to do different things frequently. I need to change it up a lot. It’s partly why I’m moving, and it’s partly why I’m running a business.

What do you appreciate the most in your friends?

Showing up is a huge one. I really appreciate it and it doesn’t even have to be physically showing up. Being able to pick up the phone or text or reach out in some way? I think that is such an amazing thing because we’re all busy all the time.

Your chief characteristic?

Other than impatience? Just kidding. My chief characteristic is probably my sense of humor, and my almost-too-much willingness to say yes to things.

What skill do you wish you possessed?

I wish I was better at accounting. Thankfully we can hire someone to do that work. There’s so much to know around that, and tax law, and I wish I were more informed.

I would love to know how to scuba dive, too.

Your most impactful book?

. That was the book that taught me I can work for myself and have a different life. The idea is to set your life up so you can minimize the amount of hours you have to actually do the thing you do to make money, so you can live the life you want to live.

What defines success?

Waking up in the morning and feeling excited about the day.

When is confidence lost?

When people say no, when ideas aren’t validated, and when people ignore you. The older I get, the less these bother me, but when I was younger, my confidence would be shot and it would be hard to get back up and move on. I’m really lucky to have a strong support system and years of experience, so it’s rare [when] my confidence is lost.

Which buzzword is exhausted?

Probably diversity. I think people use the word diversity incorrectly. They use the word diverse to mean people of color—diversity is much broader. It’s a buzzword at this point. It’s nice that they’re starting to use it to include inclusion and belonging.

What virtues do others have that you don’t?

I’d say patience, again. I want to do all the things right now. Completely unrealistic, and I try to learn from others when they look at me like I’m a crazy person.

What impact do you want to leave behind?

I’d like to leave the world a little bit kinder and more empathetic. Being human can be really freaking hard.

What’s the biggest problem tech is failing to solve?

Equity and climate change. SV is the land of disruption, but unless it makes money, there doesn’t seem to be as much of a real push to make change. Seeing the level of homelessness, illness, pain, and suffering among the wealthiest and most disruptive of populations is hard to comprehend. And what makes matters worse is that the success of tech companies have exacerbated the problem. Media coverage is plenty, and local government is stepping in but I haven’t seen tech leaders doing more to address the issue.

Illustration:��.

This was the rule for a few dinners that went to when moving friends from “Twitter to IRL.” Fast forward, those friends are some of her closest ones. Setting herself up for conversations like that, it seems, helps get her away from one of her biggest pet peeves: another post on Medium about quitting tech.

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Marshall is working on special projects with , previously worked as a director of platform at , and was also a co-founder of .

In this Proust Goes Tech, we learn about how her synesthesia is a strength and a weakness, the story behind her pinned tweet, and why she doesn’t believe in the concept of work-life balance.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

Within tech, I’d probably be starting another company. I think a lot about empathy at scale, and how we scale product decisions to take into account emotional behaviors and consequences.

I have synesthesia, which helps me visualize time. I walk through time; it’s super weird. It helps me visualize frameworks and networks—the plumbing of a company. I became the go-to person to learn the ins-and-outs of how everything was moving.

Your main fault?

I love to execute. On top of that, I’m a control freak; I tend to be obsessed to make sure everything is done perfectly. If there’s no framework or best practices sort of model for balance that can guide me, I get super overwhelmed.

I’m also very prone to burnout, which is not unique to me. It applies to both work and life. I think it’s my main fault and has led to probably the most painful parts of my work and life. I can say I have other faults, like lack of patience. I ultimately just think the ability to balance is my fault.

The quality you most desire in a tweet?

Relatable, clever, and funny. I hate tweets that shit on other people, subtweets can be funny if they’re insightful. If it’s something people need to hear, great.

I don’t wanna hear about crypto, or the latest Medium post about quitting tech and leaving SF, or whining how much this city sucks.

Tech gives so much opportunity in this world. Whether you hate it or not, there’s a reason you joined in the first place. Tech has changed a lot; whining is not productive.

A lot of the best tweeters have swim lanes they stay in.

Your idea of misery?

A world where there’s a lack of direction. Or a universe without any frameworks or rules by which to cut the road. It would be really hard for me to intake anything.

Also, a crowded world. It’s overstimulation for me.

The final one: a world in which someone is constantly questioning my integrity.

What do you appreciate the most in your friends?

Your chief characteristic?

Empathy. I am very aware of emotions, and it is natural for me to cater to the people around me. I have a really tough time not thinking about things in some empathetic manner.

I’m very objective at my job, my focus is entirely on our extended community and how we leverage the people in our community. Be it new programs for founders, be it creating access for people, it’s a privilege to do what we do in venture.

What skill do you wish you possessed?

Your most impactful book?

This is totally unrelated to tech.. It’s all around this question on what’s the deeper order of beauty and nature. It’s no accident that there’s a ton of similarities in math and physics and geometry in what we find aesthetically pleasing.

What defines success?

Doing something I love that is meaningful to others in the world. I am not driven by the fear of failure. I am driven by the fear of spending my life succeeding at things that don’t help humans, community, or the world.

.

When is confidence lost?

When trust is broken, personally and professionally. People rarely act maliciously. Often times, there’s an explanation, and I always operate with giving the benefit of the doubt if someone repeatedly decides to prove me wrong.

It gets easier as we get older.

Which buzzword is exhausted?

Disruption. We invest in things that change; I don’t understand why that’s a novel concept. It is no longer disrupting, because by nature we are in an industry that focuses on change.

What virtues do others have that you don’t?

Moderation. When I commit to something, I’m all in. I’m gonna do it to the best of my ability. I’m not great at doing things half-ass or half-committed. I don’t know if that’s moderation or if that’s temperance. I just know that I don’t know what it is like to pace myself. I’m learning.

It’s something I want to be better at.

What impact do you want to leave behind?

I think it’s two things. [First], that pinned tweet again. I want to spend my life succeeding at things, working on things that help the community, and the world.

But when I think directly about what that means, it’s how we create access and opportunity for those who are currently not part of the tech ecosystem. Growing up Latina, my mom is from Mexico City ⁠— I just think about it a lot personally.

What’s the biggest problem tech is failing to solve?

The compounding creation of moral problems while the number of companies racing to outperform each other increases. Solutions for these problems are built with more tech, and it’s a compounding problem.

For example, social emotional health. What we bring into kids’ lives has changed. With social media, we think about productivity, achievement, and growth, but I don’t think our industry is in a place yet where we’re fully taking into account the repercussions of what we’re doing.

As you have more and more companies that are in the picture, it leaves real room for possible outcomes. Because right now, the race is about growth.

Illustration:��.

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To her that means having a set of canned responses on how to say “no” on standby, drinking wine on Tuesdays, and sometimes snoozing the alarm even if a productive morning was in the books.

Choosing to slow down has helped “bring clarity” to her current job as the CEO of , a Toronto based startup that helps people make wills online, without seeing a lawyer. Beyond that, Bury is a board member for Save The Children Canada, and was once retweeted by Oprah.

In this Proust Goes Tech we chat with Erin to learn about how her grocery store job helped her be a better leader, her issue with The Office, and why her husband calls her Mary Poppins.

The interview has been edited for brevity and clarity.

What would you otherwise be doing right now?

I would probably be a tech journalist. I’m a journalism graduate and spent a couple years on the founding team at , which is one of Canada’s top startup publications. I saw that the skills journalism taught you, like writing, specifically and learning to interview people, was really helpful regardless of what career path you went on.

I think being a journalist is basically [taking] a masterclass in becoming a great entrepreneur because you just literally talk to, hundreds of entrepreneurs who are doing cool things.

I found it inspiring daily to hear about those ‘Aha’ moments that led people to start their companies, because it really taught me that inspiration can come from the most unlikely of places. And that, everyone’s origin story is different and everyone’s path to success is different.

Also, as a founder, the strongest thing you have going for you is your story.

Your main fault?

I think the biggest thing that I struggle with, and the thing that I know I need to improve, is having difficult conversations. I’ve always been the kind of person who shied away from confrontation, or from having difficult conversations. And when I was a teenager I had to call in sick to my high school job at the grocery store as a cashier. I would make my mom do it for me. Yeah. And when I had to resign from a job once, I was physically ill for days leading up to telling them, because I was so scared about having that conversation.

Now, it’s not as much as an employee having to have tough conversations with a boss or with HR, it’s more about having tough conversations with team members.

And inevitably, you have to have tough conversations when you’re running a team. And that could be everything from letting someone go, to having a conversation about performance and giving them constructive feedback, to putting someone on an improvement plan.

So I definitely know that those conversations still give me competition and give me a lot of anxiety, but they’re necessary.

The quality you most desire in a tweet?

So easy, it’s humor. There’s nothing better than a hilarious tweet thread and meme I love. I think especially when there’s so much heaviness today. There’s a lot of heavy content on Twitter and there’s so many great political discussions and conversations around gun control; you see them happening daily. But I use Twitter for its humor.

Your idea of misery?

My light version is a world without pizza, because I love pizza more than anything in the world. But to me, misery is professional boredom. When I watch movies or shows like The Office, I think that living that would be my ultimate doom. I hate being bored, I thrive off of being challenged, which is why I’m attracted to working a career like journalism which literally every day is different by nature.

The Office is fun to watch, not fun to live.

What do you appreciate the most in your friends?

Some of my friends have a similar careers, like one of them works with me at a wine tour business I run as a side gig. So those are the friends I appreciate that identify with my day to day.

Then I have friends that have absolutely nothing to do with that world. And they’re my escape. They have completely different jobs. They can’t identify with my job and I always leave get togethers with them feeling refreshed. You kind of live in this bubble as a founder, being on 24/7. Again, I think it’s the hustle porn trend and there’s a sense of guilt that you’re not working on your business. When I have dinner with them, I feel like we’re completely refreshed and I’ve taken a vacation.

Your chief characteristic?

Positivity. My husband, who is also the co-founder of Willful, always calls me Mary Poppins because he says he has never met someone who is so unfailingly positive all the time. It’s definitely something I got from my mom.

If I see my friend go through a break up or a job loss, I say let’s cry today but tomorrow I’m going to call you about next steps and why this was a good thing.

What skill do you wish you possessed?

The first entrepreneur [who] I worked for, she told me that I was a bad judge of character. I always like to see the best in people, I have a really hard time seeing people for what they really are. I assume the best in people, and usually that’s great quality but I think I get taken advantage of sometimes. I wish I had the ability to see people for what they truly are and was a better judge.

Your most impactful book?

The most impactful book I read in a business context is , a New York Times reporter. It’s all about habit formation in people and how habits can be incorporated into your business to be more successful. It’s really fascinating in understanding human nature.

What defines success?

It would be constantly being challenged and learning new things. You know, I think, after five years running of my marketing agency, I went on my honeymoon. We went on our honeymoon for three weeks to Australia, New Zealand, and Fiji. And before I left, I said to the team that I’m going to try and take time off, but if there’s anything urgent, you know, send me a note. And for three weeks, no one reached out to me. And I kind of realized that I had made myself needed, but not necessary in the organization. And that there was nothing left for me to do, there was my job was done. I realized I’m not challenged anymore. I’m not faced with a ton of obstacles. This is a well oiled machine. And that means it’s time to move on. Other people might consider success to be, you know, staying in that job for 20 years and running it smoothly.

So the first indicator of success is definitely, to me, at least constantly learning and feeling like you are challenged constantly and always feeling a little bit stressed out that you don’t know everything.

When is confidence lost?

I think to me confidence is lost when you don’t feel like an expert at something that you usually feel like an expert at.

Which buzzword is exhausted?

Oh my god, I have to say this all the time, and it drives me crazy: CAC. Customer acquisition cost. It sounds odd and like I’m cursing. When I say it, my mom is like “Pardon?” It’s not exhausted as a concept because it’s just a basic fundamental of running a strong business. But the acronym? Especially when said verbally? I think it’s definitely exhausted.

What virtues do others have that you don’t?

Patience. I feel like having a smartphone has actually made me a less patient person. And I’m sure a lot of people can identify with this, because anyone under the age of 40 probably can. I can’t stand in line idle for more than 30 seconds without looking at my phone. I like I just have to have constant stimulation. And I think it’s a weakness of our generation that we can’t just simply be.

What impact do you want to leave behind?

Being known as someone who helped other entrepreneurs find their footing. My legacy that I want to have is that I’m someone [who] people would say took time out of their day to help those that were just coming up in the industry behind them. And that I was a helpful person that helped advance the careers of other entrepreneurs.

What’s the biggest problem tech is failing to solve?

Tech addiction. I think it’s a problem that was created by technology. And it’s a problem that there is an onus on tech firms to contribute to solving, but it’s inherently at odds with their business models. When you look at companies like , their business model relies on us using their technology as often as possible. While I believe that they’re doing a good job of saying that they want to help us use their tools, less, I think it’s a PR play. I don’t think it’s actually fundamentally one of their core values, their core values are to make us use their product as much as possible to increase their bottom line.

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