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Alyssa Rapp of Surgical Solutions: “Start small”

…Oh it’s so fun to start your own company! It’s gratifying, you control your own destiny, great job variety, you get to have an idea and inspire people to see it come to life. Founding your own company is gratifying, challenging, can be lucrative, inspiring, fun, self-reliant, all that good stuff is why women should […]

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…Oh it’s so fun to start your own company! It’s gratifying, you control your own destiny, great job variety, you get to have an idea and inspire people to see it come to life. Founding your own company is gratifying, challenging, can be lucrative, inspiring, fun, self-reliant, all that good stuff is why women should found their own companies.


As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Alyssa Rapp.

Since January 2018, Alyssa has served as the CEO of Surgical Solutions, a Chicago-area based Health Care company. Alyssa is also a lecturer-in-management at Stanford University’s Graduate School of Business and an Adjunct Professor of Entrepreneurship at the University of Chicago’s Booth Business School. From 2005–2015, Alyssa served as the founder & CEO of Bottlenotes, Inc., the leading interactive media company in the U.S. wine, craft beer, and artisanal spirit industries.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I started my career in politics as a Finance Director for U.S. Congresswoman Jan Schakowsky and after that I ended up going to business school at Stanford where I followed by entrepreneurial passions and pursuits and from there, I ended up stating my first company called Bottlenotes which was a dot.com in the wine space and it was a twisty and turning journey and a great learning experience and a pivot in between from ecommerce to media play. Learned a ton. A lot. Caught a couple breaks. Lost a couple breaks. Just learned a ton. And from that tenure on, I took three years at AJR Ventures to do advisory work for private equity back companies and then I stepped into the role at Surgical Solutions in Chicago, a health care services company, was then owned by Sterling Partners in January 2018. I’ve been at the role for the last three years.

Can you share the most interesting story that happened to you since you began your career?

The most interesting thing I have done in my career is to pivot twice. Once from politics into entrepreneurship and then highly regulated alcohol & beverage into healthcare. People joke, what is the relationship between those two: Low tech enablement and highly-regulated industries that either indirectly or directly impact people’s daily lives I think is the consistency. I think the most interesting things are the pivots.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I started out at Surgical Solutions, at one of my first hospital site visits I had just come off a red-eye and I was wearing super high high-heels in a hospital where everybody wears sneakers or clogs. And I still had to put on the bunny suit and for some reason — -I had not packed any other shoes with me — and here I am walking thru the hospital, a rookie CEO in health care walking around in scrubs and high heels.

None of us can achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I am extremely fortunate to count a handful of mentors that I can credit with helping to provide me with coaching that influenced my decision making at crucial junctures in my career. I talk about several of them, including my mother, Fay Hartog Levin, in the chapter “On Mentorship” in Leadership and Life Hacks. Joel Peterson of Peterson Partners is one of the most influential mentors to me as such; I have endless gratitude to him for the wisdom and support he has provided me in ways small and very large. His book on the 10 Laws of Trust is a must-read.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Well, it’s no secret I’m a massive Ayn Rand fan and love more than almost any book I’ve ever read, “Atlas Shrugged.” The inherent tension between a rugged individualist and I, the human being, compassion, and civic duty, are three things that are in congruous, and I wrestle with those on a day-to-day basis in terms of which should prevail. That’s probably the book that most profoundly impacted me.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

One of the best pieces of advice I’ve ever been given came from Joel Peterson, my mentor at Stanford Business School and the chairman of JetBlue, whom I talked about in my book, Leadership & Life Hacks under Life Hack #65: You’re not looking for daily balance. You’re looking for episodic balance. Here’s what “episodic balance” means to me. There are going to be times I spend a lot of time with my kids and fill up that well with love and experience and connection. For example, we’ll spend all of spring break together skiing, or we’ll spend a week to ten days visiting friends around the country or elsewhere in the globe during the summer. During those times, my career takes a backseat. Work doesn’t go away completely — it gets compressed like a toothpaste tube. I might push it down to an hour or two a day, knowing that it’s time for me to fill the well as a mom and wife.

And then there are going to be many days where work takes the driver’s seat. When I fly for work, which is often weekly, day trips are my favorite: 6 am flight out and back to see a current or prospective client, and head right back. No matter if I am gone for one day or two (as I try desperately hard not to be away from our girls for more than one night in a given week, if any), when I’m on the road, checking in with Facetime and texts, getting photos from our childcare professional about how they are doing. But basically, for 18, 24, or 36 hours, I’m not there. I must trust that the infrastructure we’ve put in place — childcare, grandparents, after-school activities, etc. — is strong enough to hold. Hal and I always strive to be away at different times so the girls are never without both of us — but even so, three to five days a year, we are both gone at the same time. (The only silver lining is if and when by the fates, we are away in the same place!)

Still, the fact that we’ve been able to work it out so at least one of us is with our girls, ~360 days a year? That’s episodic balance. It’s not daily, because I can’t be with my kids all day, every day. Nor can Hal. Nor can I be at my job 24/7 365 days a year. I strive to create balance in countless other ways, big and small, across the varied aspects of my life. I work to make sure the mom part of me is well tended, as are all the other parts.

This simple concept from Joel has been an essential building block in my life and career.

How have you used your success to make the world a better place?

Civic Duty. I have been on boards and non-profit boards the entire time I’ve been a working professional and a CEO. I feel like you have to give back, in time, as well as resources. It’s really important to pick issues that you care about. Mine happen to be around early childhood education, and the arts and it’s a really wonderful thing to have that clarity of purpose. And I’m passionate about public housing and that’s really been a filter thru which I choose the board work I do.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

If we take a leap of faith that women are as talented and creative and capable as men at starting companies, if not more so, then you have to look at the structural environment around how companies get created and companies get created when passionate people, and all women, have great ideas, inspire people to follow them, and then get the support, economic and otherwise, to get things off the ground. I’ve done it more than once in my career. And what I can tell you is, there are more men who are investors today than women and therefore, you know, people, it has taken time, as women investors have become more and more the norm in private equity and top venture capital and public firms, for that sea change to begin. Does that mean women can only take money from women? No, I have been started and been backed, whether it’s been venture capital backed or private equity backed companies with tremendous men who have believed in me, sponsored me, and helped me get from A to B. I have been incredibly fortunate in people’s faith and sponsorship. Now, I think if women find it hard to launch companies, taking it as a leap of faith that they have great ideas, potentially it is because you need a network of people to back you and perhaps, they don’t have a network of people who look like them, think like them, etc.., and have the resources to do it. But that’s changing. I think it’s really a great idea is not enough. You need a great idea and the backing and so it’s access to capital, access to informal and formal networks that provide that capital.

Can you share with our readers what you are doing to help empower women to become founders?

Easy answer. I started a class at the University of Chicago’s Booth Business School a year and a half ago called “Women as CEOs, Investors, Directors, and Executives” and I teach a class, and have taught a class at Stanford Business School, particularly in the past year called “Managerial Skills” and I take a personal interest and relationship with students of mine who want to found companies. The first course I shared here was all about inspiring women to be leaders, whether of their own entity or someone else’s and take calls and help them connect with people who will help them achieve their goals as entrepreneurs. So I walk the walk in that department. I am also with my family a seed-stage investor in several seed-stage venture funds that invest in women and non-obvious founders like Ali Rosenthal’s Leadout Capital or Jessica Yagan’s Impact Engine or Sam Yagan’s Corazon Capital. On a personal note, the only angel investing that I do directly myself is in women founders.

This might be intuitive to you but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

Oh it’s so fun to start your own company! It’s gratifying, you control your own destiny, great job variety, you get to have an idea and inspire people to see it come to life. Founding your own company is gratifying, challenging, can be lucrative, inspiring, fun, self-reliant, all that good stuff is why women should found their own companies.

Ok super. Here is the main question of our interview. Can you please share 5 things that can be done or should be done to help empower more women to become founders? If you can, please share an example or story for each.

1. First thing to empower more women to become founders is access to seed-stage capital. Women who have gone to business school who have access to vary angel investing networks, etc. but that first half a million or million dollars raised in some way, the hardest. Providing access to angel investing networks for women by woman in one idea.

2. Encouraging more and more women to become investment professionals. I agree with Gina Davis, “If you can see it, you can be it” and so that idea of having more women [inaudible]. There has been a great movement in Silicon Valley by friends of mine like Emily Melton and several others at Threshold Ventures who are leading the charge of diversity in the board room and on Sand Hill Road in Silicon Valley and so having more women investment professionals will change some of those previously discussed dynamics as well.

3. Teaching entrepreneurship more readily in undergrad and graduate education is important. It’s a skill, it’s an art, and it requires magic and that, I know that. But there are je ne sais quoi, some building blocks like how to put together a business plan and what do you need for extraimperial finance that can be taught, that can be a building block.

4. Start small. We try to do entrepreneurial things for our daughters who are 8 and 5. You know, make bracelets, sell bracelets. Bake cookies, sell them. Do things that can teach entrepreneurship on a very small scale.

5. Last but not least, number five, I firmly believe in this idea that it’s in the air. You can feel it when you are in Silicon Valley. People don’t ask the question of why are you doing something, they ask why wouldn’t you? And that’s because it’s filled with great champions, mentors, and people who have done it before. The more role modeling, the more sharing of entrepreneurial role models like Authority Magazine, doing all that to really continue to spotlight and highlight the promise of women as entrepreneurs will continue to make it more and more obvious that it’s a path women can pursue.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I think Ariana Huffington has built a fascinating career and platform and I’d be delighted to have breakfast with her.

How can our readers further follow your work online?

AlyssaRapp.com or my weekly newsletter, #HacksTheNewsletter, or they can buy my book “Leadership & Life Hacks” on Amazon. Or follow me on social: facebook.com/alyssarapp, Instagram.com/alyssajrapp, Twitter @AlyssaRapp, LinkedIn

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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