Startup Parent

#030 — Motherhood, Tech Startups and Giving Up Control with Sara Mauskopf of Winnie 

Motherhood can be a real revelation for those of us with Type A personalities. As much as we would like to control our own destiny and schedule our lives according to a predetermined plan, parenting simply doesn’t work that way. Life doesn’t work that way. And neither do startups.

Sara Mauskopf was already dealing with the surprises that come from being a new mom back at work when she got the idea for a tech startup of her own. With the financial means to move forward and a supportive partner in her husband, Sara realized that while it was not an ideal time to walk away and become an entrepreneur, it would never get any easier. She would never have fewer responsibilities or less on her plate, so she took the leap. Together with her co-founder, Sara created Winnie, a companion app for modern parents.

And then her husband was diagnosed with cancer. Resigned to the fact that the new company might die without her, Sara signed off for two weeks to focus on her husband. But when she returned to work, the Beta version of the app was ready to launch. The team had been productive without her, facilitated by the flexible, family-friendly environment in place at Winnie.

Today Sara shares the inspiration for her venture, explaining how the app offers parents timely, personalized information as well as answers to basic parenting questions. I ask her about making the decision to found a tech startup as a new mom and establishing the family-friendly work environment at Winnie. Sara discusses her husband’s illness, how she used blogging to ask for help and process in real time, and how the experience changed her perspective on work. Listen in for Sara’s insight on the compatibility between motherhood and startups and her advice around mentorship and networking with women in tech.

FULL SHOW NOTES:

Get the complete show notes with episode quotes, photos, and time stamps at www.startuppregnant.com/030.

EPISODE SPONSOR & SPECIAL OFFER:

Thank you to the sponsor of this episode: Aeroflow Breastpumps. They are dedicated to making the hassle of getting your breast pump a little bit easier—actually, a lot easier! Head to www.aeroflowbreastpumps.com/startup to have them help you qualify for a free breast pump through insurance.

All of our sponsor offers are available on our website for you to grab the perks and discounts offered to podcast listeners: http://startuppregnant.com/sponsors.

LEARN MORE ABOUT SARA MAUSKOPF:

Sara Mauskopf is the co-founder and CEO of Winnie, a venture dedicated to making parents’ lives easier through technology. Sara graduated from MIT with a degree in computer science and engineering and went on to work as one of the early employee at Twitter. Her impressive resume also includes positions with Silicon Valley powerhouses including Google, YouTube and Postmates.

• Winnie
• Winnie on Twitter
• Winnie on Facebook
• Winnie on Pinterest
• Winnie on Instagram
• Sara on Medium

RESOURCES MENTIONED IN THIS EPISODE

• Tech Ladies
• Women in Technology
• Female Founders Fa

#029 — Unifying Work and Family with Amber Anderson of MORE

There are women who pursue entrepreneurship because they have a creative vision to change the world. And then there are women who pursue entrepreneurship because they have to.

Amber Anderson was sitting in a conference room with her colleagues, talking about the George Zimmerman trial. As her peers expressed disbelief in the not guilty verdict—and then went right back to their work—Amber put her hand on her pregnant belly and thought, “What did I do?”

Concerned about bringing a child into a world where an African American child was murdered, and no one seemed to care, Amber and her husband Kai came up with a plan to be as involved in their son’s life as possible: Kai would stay home with the baby, and Amber would continue at her job in tech.

But then her water broke at just 31 weeks, and Amber’s son Kayson spent three weeks in the NICU. When Amber’s maternity leave was up, she decided she simply could not choose between work and family. She wanted to be there for her son, so she chose entrepreneurship out of necessity—to create a new model that would weave work and family together.

Today Amber shares her family systems, explaining how she and her husband structure their days around their son. I ask her how she came to start multiple companies and how parenting has changed the way she shows up at work. Amber discusses the idea behind her latest venture, The New More, and what conference organizers can do to accommodate women. Listen in to understand the concept of a necessity entrepreneur and hear Amber’s take on how to evaluate success.

FULL SHOW NOTES:

Get the complete show notes with episode quotes, photos, and time stamps at www.startuppregnant.com/029.

EPISODE SPONSOR & SPECIAL OFFER:

Thank you to the sponsor of this episode: Meet Edgar! Grab your free two-week trial of Meet Edgar, a social media scheduling tool that allows you to create content once and re-use it as much as you need, at http://ed.gr/startuppregnant.

All of our sponsor offers are available on our website for you to grab the perks and discounts offered to podcast listeners: http://startuppregnant.com/sponsors.

LEARN MORE ABOUT AMBER ANDERSON:

Business strategist and thought leader Amber Anderson is the founder of Kayson, a business consulting agency that works with innovators, entrepreneurs, VCs and business owners to thoughtfully develop and strategically launch new products and services. Amber is also the co-founder of MORE, a community that is redefining balance by helping working parents advance their careers—without leaving their families behind.

• The New More
• The New More Podcast
• The New More on Facebook
• The New More on Twitter

THE STARTUP PREGNANT PODCAST & HOST:

• Startup Pregnant
• Startup Pregnant on Facebook
• Startup Pregnant on Twitter
• Sponsor the Podcast
• Sponsor the Podcast

#029 — Unifying Work and Family with Amber Anderson of MORE

There are women who pursue entrepreneurship because they have a creative vision to change the world. And then there are women who pursue entrepreneurship because they have to.

Amber Anderson was sitting in a conference room with her colleagues, talking about the George Zimmerman trial. As her peers expressed disbelief in the not guilty verdict—and then went right back to their work—Amber put her hand on her pregnant belly and thought, “What did I do?”

Concerned about bringing a child into a world where an African American child was murdered, and no one seemed to care, Amber and her husband Kai came up with a plan to be as involved in their son’s life as possible: Kai would stay home with the baby, and Amber would continue at her job in tech.

But then her water broke at just 31 weeks, and Amber’s son Kayson spent three weeks in the NICU. When Amber’s maternity leave was up, she decided she simply could not choose between work and family. She wanted to be there for her son, so she chose entrepreneurship out of necessity—to create a new model that would weave work and family together.

Today Amber shares her family systems, explaining how she and her husband structure their days around their son. I ask her how she came to start multiple companies and how parenting has changed the way she shows up at work. Amber discusses the idea behind her latest venture, The New More, and what conference organizers can do to accommodate women. Listen in to understand the concept of a necessity entrepreneur and hear Amber’s take on how to evaluate success.

FULL SHOW NOTES:

Get the complete show notes with episode quotes, photos, and time stamps at www.startuppregnant.com/029.

EPISODE SPONSOR & SPECIAL OFFER:

Thank you to the sponsor of this episode: Meet Edgar! Grab your free two-week trial of Meet Edgar, a social media scheduling tool that allows you to create content once and re-use it as much as you need, at http://ed.gr/startuppregnant.

All of our sponsor offers are available on our website for you to grab the perks and discounts offered to podcast listeners: http://startuppregnant.com/sponsors.

LEARN MORE ABOUT AMBER ANDERSON:

Business strategist and thought leader Amber Anderson is the founder of Kayson, a business consulting agency that works with innovators, entrepreneurs, VCs and business owners to thoughtfully develop and strategically launch new products and services. Amber is also the co-founder of MORE, a community that is redefining balance by helping working parents advance their careers—without leaving their families behind.

• The New More
• The New More Podcast
• The New More on Facebook
• The New More on Twitter

THE STARTUP PREGNANT PODCAST & HOST:

• Startup Pregnant
• Startup Pregnant on Facebook
• Startup Pregnant on Twitter
• Sponsor the Podcast
• Sponsor the Podcast

#028 — Learning to Drop the Ball with Author and Activist Tiffany Dufu

If you’re still trying to figure out how to do it all—to be great mom, a great wife, and a great employee—and you’re starting to realize that it just isn’t possible, it may be time to drop a ball or two.

Tiffany Dufu had a reckoning on her first day back at work from maternity leave. After a hectic day running from meeting to meeting, she realized she had forgotten to stop and pump. And the reality of being a working mom hit her as the milk seeped through her blouse.

Resentment and anger showed up that evening as she listened to her husband come home from work, and she thought through all of the things she had done to make his life easier and more predictable that day, from picking up the dry cleaning to putting a dinner plate in the refrigerator for him. It didn’t take long for Tiffany to realize that she had to renegotiate the terms of her marriage and redefine what it means to be a ‘good’ wife and mother.

Tiffany took the time to get clear on what matters most to her and what she does really well, using that intelligence to decide which items on the to-do list were really necessary and which balls could be dropped. Today she explains the social conditioning that makes women think they have to do it all, what you can do in that moment of overwhelm, and how to determine your mission. I ask her how she initiated conversation about equity with her husband and why she has eliminated to-do lists from her life. Listen in for Tiffany’s insight around the urgency of having women in leadership and the value of investing in community.

FULL SHOW NOTES:

Get the complete show notes with episode quotes, photos, and time stamps at www.startuppregnant.com/028.

EPISODE SPONSOR & SPECIAL OFFER:

Thank you to the sponsor of this episode: HippoGive! HippoGive is a new app that donates your change by rounding up your everyday transactions to the nearest dollar and gives it to the charities and non-profits of your choosing.

If you’ve been wanting to donate to Planned Parenthood, the ACLU, or disaster relief you can use this app and it’s a piece of cake. Go to www.startuppregnant.com/charity to learn more about how HippoGive is currently matching all of your first-time donations up to the first $50!

All of our sponsor offers are available on our website for you to grab the perks and discounts offered to podcast listeners: http://startuppregnant.com/sponsors.

LEARN MORE ABOUT TIFFANY DUFU:

Tiffany Dufu is the author of Drop the Ball, a memoir and manifesto that seeks to help women cultivate the single skill they really need to thrive—the ability to let go. Tiffany was part of the launch team for Lean In and serves as Chief Leadership Office to Levo, one of the fastest growing millennial professional networks. She was named to Fast Company’s League of Extraordinary Women, and she serves on the board of Girls Who Code and Simmons College.

• Tiffany’s Website
• Drop the Ball: Achieving More by Doing Less by Tiffany Dufu
• Drop the Ball on Audible

RESOURCES MENTIONED IN THIS EPISODE:

• Lean In: Women, Work, and the Will to Lead by Sheryl Sandberg
• The 7 Habits of Highly Eff

#028 — Learning to Drop the Ball with Author and Activist Tiffany Dufu

If you’re still trying to figure out how to do it all—to be great mom, a great wife, and a great employee—and you’re starting to realize that it just isn’t possible, it may be time to drop a ball or two.

Tiffany Dufu had a reckoning on her first day back at work from maternity leave. After a hectic day running from meeting to meeting, she realized she had forgotten to stop and pump. And the reality of being a working mom hit her as the milk seeped through her blouse.

Resentment and anger showed up that evening as she listened to her husband come home from work, and she thought through all of the things she had done to make his life easier and more predictable that day, from picking up the dry cleaning to putting a dinner plate in the refrigerator for him. It didn’t take long for Tiffany to realize that she had to renegotiate the terms of her marriage and redefine what it means to be a ‘good’ wife and mother.

Tiffany took the time to get clear on what matters most to her and what she does really well, using that intelligence to decide which items on the to-do list were really necessary and which balls could be dropped. Today she explains the social conditioning that makes women think they have to do it all, what you can do in that moment of overwhelm, and how to determine your mission. I ask her how she initiated conversation about equity with her husband and why she has eliminated to-do lists from her life. Listen in for Tiffany’s insight around the urgency of having women in leadership and the value of investing in community.

FULL SHOW NOTES:

Get the complete show notes with episode quotes, photos, and time stamps at www.startuppregnant.com/028.

EPISODE SPONSOR & SPECIAL OFFER:

Thank you to the sponsor of this episode: HippoGive! HippoGive is a new app that donates your change by rounding up your everyday transactions to the nearest dollar and gives it to the charities and non-profits of your choosing.

If you’ve been wanting to donate to Planned Parenthood, the ACLU, or disaster relief you can use this app and it’s a piece of cake. Go to www.startuppregnant.com/charity to learn more about how HippoGive is currently matching all of your first-time donations up to the first $50!

All of our sponsor offers are available on our website for you to grab the perks and discounts offered to podcast listeners: http://startuppregnant.com/sponsors.

LEARN MORE ABOUT TIFFANY DUFU:

Tiffany Dufu is the author of Drop the Ball, a memoir and manifesto that seeks to help women cultivate the single skill they really need to thrive—the ability to let go. Tiffany was part of the launch team for Lean In and serves as Chief Leadership Office to Levo, one of the fastest growing millennial professional networks. She was named to Fast Company’s League of Extraordinary Women, and she serves on the board of Girls Who Code and Simmons College.

• Tiffany’s Website
• Drop the Ball: Achieving More by Doing Less by Tiffany Dufu
• Drop the Ball on Audible

RESOURCES MENTIONED IN THIS EPISODE:

• Lean In: Women, Work, and the Will to Lead by Sheryl Sandberg
• The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change by Stephen R. Covey

 
THE STARTUP PREGNANT PODCAST & HOST:

• Startup Pregnant
• Startup Pregnant on Facebook
• Startup Pregnant on Twitter
• Sponsor the Podcast
• Sponsor the Podcast

#027 — Reframing the Unexpected as Opportunity with Logz.io VP of Sales Bridget Gleason 

The one thing Bridget Gleason knew, beyond a shadow of a doubt, was that she wanted to be a stay-at-home mom, providing her kids and her family with an incredible life.

And then the universe handed her something completely different.

When Bridget’s boys were one and three, her husband left—and she had no choice but to go back to work. So she interviewed for a sales position, negotiating a flexible part-time schedule in which she would be compensated based on performance rather than hours spent in the office.

Motivated to spend as much time with her sons as possible, Bridget’s unanticipated status as a single mother afforded her a crash course in productivity, teaching her to prioritize the handful of to-dos that were most impactful. Going back to work also taught her to reframe the unexpected as a gift: She could have a rewarding career AND be a good mom. She didn’t have to choose one or the other.

Today Bridget shares her resilience in the face of uncertainty, explaining how that process continues to this day. I ask her about the role emotions play in her work life and how she defies expectations to behave a certain way as VP of Sales. Listen in for Bridget’s advice around prioritizing self-care, ‘sharing the real’ when your kids are struggling, and reframing surprises as opportunities rather than obstacles.

FULL SHOW NOTES:

Get the complete show notes with episode quotes, photos, and time stamps at www.startuppregnant.com/027.

EPISODE SPONSOR & SPECIAL OFFER:  

Thank you to the sponsor of this episode: Taskerly! They’re a virtual assistant company that helps busy parents and entrepreneurs get more done at work by doing the things you can outsource of don’t have time for. Check them out at www.taskerly.co and mention the Startup Pregnant Podcast to get 10% off of your first three months working with them.

 All of our sponsor offers are available on our website for you to grab the perks and discounts offered to podcast listeners: http://startuppregnant.com/sponsors.

 
LEARN MORE ABOUT BRIDGET GLEASON:

Bridget Gleason is the Vice President of Sales at Logz.io, the world’s most popular open-source log analysis platform. Her strengths lie in accelerating sales for startups and early-stage SaaS and PaaS technology companies, delivering significant revenue increases, forecast predictability and customer retention. An industry thought-leader, Bridget is a sought-after presenter at sales, leadership and women’s conferences, and she is most recognized for her phenomenal success in building and leading high-velocity sales organizations.

Logz.io

Bridget on LinkedIn

Bridget on Twitter
 

RESOURCES MENTIONED IN THIS EPISODE:

Solve for Happy: Engineer Your Path to Joy by Mo Gawdat

THE STARTUP PREGNANT PODCAST & HOST:

Startup Pregnant

Startup Pregnant on Facebook

Startup Pregnant on Twitter

Sponsor the Podcast

Sponsor the Podcast

#026 – Infertility, Invisibility with Anne

Do you want to be a mother?

When was the first time you were asked this question? For Anne, it was at the age of six. And so much of a woman’s identity is tied up in her answer to this question.

Anne wasn’t sure how to answer the motherhood question until she met her husband, and then the answer became a resounding yes. She wanted to have a family with this man. So they started trying a year and a half ago…

But after seeing the doctor for preliminary tests, Anne learned that she wasn’t ovulating. She was diagnosed with unexplained infertility. Now she finds herself stuck between hope and full mourning, carrying the invisible emotional weight that comes with not knowing what the future holds.

Today Anne bravely shares her fertility journey, explaining the difficult conversations surrounding her diagnosis and how the experience has impacted her business. I ask her what she wishes she had known as a young woman and how she approaches the uncertainty. Listen in for Anne’s insight around initiating conversations about infertility, taking charge of your physical and financial health, and the mental discipline it requires to keep hoping for the best.

FULL SHOW NOTES:

Get the complete show notes with episode quotes, photos, and time stamps at www.startuppregnant.com/026.

EPISODE SPONSOR & SPECIAL OFFER:

Thank you to the sponsor of this episode: Aeroflow Breastpumps. They are dedicated to making the hassle of getting your breast pump a little bit easier—actually, a lot easier! Head to www.aeroflowbreastpumps.com/startup to have them help you qualify for a free breast pump through insurance.

All of our sponsor offers are available on our website for you to grab the perks and discounts offered to podcast listeners: http://startuppregnant.com/sponsors.

THE STARTUP PREGNANT PODCAST & HOST:

Startup Pregnant

Startup Pregnant on Facebook

Startup Pregnant on Twitter

Sponsor the Podcast

#025 – Live and Learn—Out Loud

Core values are part of a living document. They grow, change and shift in relationship to the community they guide.

And the only way to craft the ‘right’ core values is by creating a draft and shipping it out into the world to see what sticks. Scary as it may be to publish something that you know isn’t perfect, initiating the conversation by sharing the work helps identify which values resonate and which ones don’t, which ones overlap and which ones appear to be missing.

As part of my commitment to live out loud, I published the 10 Core Values of the Startup Pregnant Philosophy—knowing that the feedback I received from the community would inform their evolution. Already I can see what is really working and what needs to be added. So many of you responded to Core Value #1, In My Experience, it is clear to me that acknowledging every individual’s unique experience is at the foundation of our movement.

I also discovered that I had missed a couple of things that were important. Your feedback reminded me of the absolute necessity to put the work out into the world and then learn out loud, processing the core values through our dialogue.

If you haven’t already, join the core value conversation on the Startup Pregnant blog, and let me know what speaks to you. Let’s try on these ideas together and design the very best way to inspire and connect this powerful community of women.

FULL SHOW NOTES:

Get the complete show notes with episode quotes, photos, and time stamps at http://www.startuppregnant.com/025.

THE STARTUP PREGNANT PODCAST & HOST:

Startup Pregnant

Startup Pregnant on Facebook

Startup Pregnant on Twitter

Sponsor the Podcast

Email [email protected]

#024 — Decision-Making with Head and Heart with Bonnie Foley-Wong of Pique Ventures

Life rarely goes according to plan. 

In 2011, Bonnie Foley-Wong had just moved to Vancouver to pursue her dream job. She and her husband had plans to start a family the following year. But eight months in, Bonnie walked away from the great job with great benefits to start Pique Ventures—and getting pregnant was put on hold. 

Eventually, Bonnie felt good enough about her business to start a family, and in March of 2014 at the age of 40, she was pregnant with her daughter. At the very same time, she was starting an accelerator, securing investors for Pique Fund, and writing a book, Integrated Investing. By sheer force of will, Bonnie did her first close of fund in October, had her baby in November, and led Pique’s first investment in December. A fertile year, to say the least. 

Every step of the way, Bonnie made decisions based on head and heart, doing research when she could, but taking leaps of faith into uncertain territory. Today Bonnie shares the details of her path to entrepreneurship, exploring how pregnancy informed and impacted that journey—and vice versa. She explains the difference between Pique Venture and Pique Fund, discussing how both analysis and emotion inform her decision-making. I ask her about tapping into intuition in the workplace and how she overcame the idea that entrepreneurship was something ‘other people did.’ Listen in to learn how Bonnie created a meaningful livelihood, living by the mantra that ‘routine makes space for spontaneity.’ 

FULL SHOW NOTES: 

Get the complete show notes with episode quotes, photos, and time stamps at www.startuppregnant.com/024. 

EPISODE SPONSOR & SPECIAL OFFER:   

Thank you to the sponsor of this episode: Meet Edgar! Grab your free two-week trial of Meet Edgar, a social media scheduling tool that allows you to create content once and re-use it as much as you need, at http://ed.gr/startuppregnant. 

All of our sponsor offers are available on our website for you to grab the perks and discounts offered to podcast listeners: http://startuppregnant.com/sponsors. 

LEARN MORE ABOUT BONNIE FOLEY-WONG:  

Bonnie Foley-Wong is the founder of Pique Ventures, an

#023 — 40% of American households believe that it is bad for society if mothers work.

Because sexism is a global phenomenon, you might believe this statistic to be universal as well—but it just isn’t. In fact, this kind of maternal bias against women in the workplace is a strictly American phenomenon. Diverse cultures from deeply feminist Iceland to ‘one-child policy’ China simply do not have stay-at-home moms.

Today Sarah explains how this staggering statistic manifests itself in the our culture, from the wage gap to maternity leave policy to overt sexism on the job. I ask her about the need to dismantle the patriarchy and her experience of maternal bias in the workplace. She shares her journey from ‘cool girl’ sexism denier to fierce feminist, explaining how becoming a mother allowed her to find her power as a woman and gave her the confidence to start her own business. Listen in as we discuss the way that calling out bad behavior is shifting the world of work and how to go about changing the narrative of the young, single working mother, startup founder.

FULL SHOW NOTES:

Get the complete show notes with episode quotes, photos, and time stamps at www.startuppregnant.com/023.

EPISODE SPONSOR & SPECIAL OFFER:

Thank you to the sponsor of this episode: HippoGive! HippoGive is a new app that donates your change by rounding up your everyday transactions to the nearest dollar and gives it to the charities and non-profits of your choosing.

If you’ve been wanting to donate to Planned Parenthood, the ACLU, or disaster relief you can use this app and it’s a piece of cake. All you need to do is create an account, choose your charity and then set a weekly donation cap. Head to HippoGive.com to sign up.

All of our sponsor offers are available on our website for you to grab the perks and discounts offered to podcast listeners: http://startuppregnant.com/sponsors.

LEARN MORE ABOUT SARAH LACY:

Sarah Lacy is the founder, CEO, and editor-in-chief of investigative tech news organization PandoMedia. An award-winning reporter based in Silicon Valley, Sarah was a columnist for Bloomberg Businessweek and senior editor at TechCrunch before striking out on her own. She has fifteen-plus years of experience covering technology news and all things startups, making her a sought-after speaker at tech and business conferences around the world. Sarah is the critically-acclaimed author of several books, including the recently published A Uterus is a Feature, Not a Bug.

A Uterus is a Feature, Not a Bug: The Working Woman’s Guide to Overthrowing the Patriarchy by Sarah Lacy

Email [email protected]

Chairman Mom

Pando

Sarah on Pando

Sarah on Twitter

Sarah on Instagram

RESOURCES MENTIONED IN THIS EPISODE: 

Courtney Martin at On Being

“The End of the Cult of the Founder” in Wired

Reset: My Fight for Inclusion and Lasting Change by Ellen Pao

THE STARTUP PREGNANT PODCAST & HOST: