An Interview With Vanessa Ogle
Be One, Get One: The Power of Mentorship
Despite strides towards equality, women remain underrepresented in leadership and management roles across various sectors. In this series, we would like to discuss the barriers to female advancement in these areas and explore actionable strategies for change. We are talking with accomplished women leaders, executives, and pioneers who have navigated these challenges successfully, to hear their experiences, tactics, and advice to inspire and guide the next generation of women toward achieving their full potential in leadership and management roles. As part of this series, we had the pleasure of interviewing Alyssa Rapp, CEO of Empower Aesthetics.
Before joining Empower Aesthetics as CEO, Rapp served as the CEO of Healthwell Acquisition Corp., a special purpose acquisition company focused on businesses in healthcare technology, tech-enabled healthcare services, and tech-enabled wellness. From 2018 to 2021, she served as CEO of Surgical Solutions, a B2B healthcare services business providing non-clinical surgical services to hospitals, where she led a successful turnaround of the enterprise, driving 21% sales growth with 90% customer retention. From 2015 to 2018, Rapp served as the founder and CEO of Bottlenotes, Inc., a leading interactive media company. Before that, she served as the managing partner of AJR Ventures, a strategic advisory firm for family offices and private equity firms on market development, digital and e-commerce strategies for select portfolio companies.
Rapp serves as an independent director of Elevate Women’s Health and Health Data Movers, and an elected school board member for District 36 in Winnetka, Illinois. She is a lecturer-in-management at Stanford University’s Graduate School of Business and Adjunct Professor of Entrepreneurship at the University of Chicago’s Booth Business School. Rapp earned a B.A. in Political Science and the History of Art from Yale University in 2000 and an M.B.A. from Stanford University’s Graduate School of Business in 2005. She is the author of Amazon Bestseller, Leadership and Life Hacks: Insights from a Mom, Wife, Entrepreneur & Executive (ForbesBooks, October 2019).
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 US politics as the national finance director for a U.S. Congresswoman, then went to business school to pursue my entrepreneurial dreams. At Stanford’s graduate school of business, I fell in love with my husband and my first business idea: Bottlenotes– first, endeavoring to be the Netflix for wine, which pivoted (due to regulatory climate shifts) to a leading digital media player in the alcohol beverage space before exiting to a hedge fund in 2015. Thereafter, I spent the next two years doing advisory work for two family offices and two private equity firms in two cities (Silicon Valley and Chicago) until our second daughter turned two, under the umbrella of AJR Ventures. During this time, I also began teaching at Stanford’s Graduate School of Business. Thereafter, my husband Hal and I decided to move back to Chicago with our two young daughters to be closer to our families when my father-in-law passed away suddenly. As of January 2018, I stepped back into the CEO chair, this time as a private equity backed CEO in the B2B healthcare space for Sterling Partner, with Surgical Solutions.
Moving from the consumer internet category to B2B healthcare solutions was a major career shift, and without a doubt set the course of the next ten years of my professional life. We completed our mission at Surgical Solutions when the turnaround was complete and the company was sold to a global strategic partner in the space, Grupo Vitalmex, also owned by private equity firm, Australis Partners, in February 2020. Thereafter, I launched a special-purpose acquisition corporation (“SPAC”) in February 2021 called Healthwell, seeking to help a private technology-enabled healthcare company go public via our shell entity. At Healthwell, our world class board and team ran the SPAC like a private equity fund, reviewing and diligencing over 100+ companies in less than 24 months, pursuing letters of intent with 13. Thereafter, Shore Capital Partners asked me to step in as the CEO of Empower Aesthetics, on whose board I had served since inception for them, in December 2023. Which brings us to today. :).
Can you share the most interesting story that happened to you since you began your career?
The most interesting stories about my career, I believe, are the unexpected industry pivots. Having first left US politics for the world of entrepreneurship, and in the alcohol beverage space, and later from alcohol beverage to healthcare, and of course, moving from venture-backed to private-equity backed and public asset classes, and then back to PE, there have been numerous pivots in the past 20 years of my career. In each experience, in each transition, the challenge and opportunity has been to find “product-market fit,” and lead teams with values-based, mission-driven approaches to the outcome. In each case, we have launched or rebooted an idea (company/business offering) into the universe, where the mission, vision, and values that guided us were all shared. Thematically, one other common thread is that while I left the consumer-Internet/US alcohol beverage industry for B2B healthcare service, and the divergence in industry might seem stark, many similarities exist. Both are highly regulated industries, where the customer (patient/client) is or should come first. Both industries have been historically low-tech with high barriers to entry, and the highest of regulatory environments. Most importantly, I enjoy working in companies and leading teams where the mission to positively impact people’s daily lives is overt.
Can you share a pivotal moment in your career that significantly influenced your path to leadership?
All of the great assessment firms like my friend Andre Zafrani’s Apogee Leadership Advisors would tell you that if you review the chapters of a leader’s life from a very young age, leaders have a trajectory of leadership whose foundation begins to shine through early on in their character and life experiences. In my life, I have many people and experiences to thank as role models and mentors. First, I have had great role models of leadership throughout my entire life, from my entrepreneurial, Dutch, Holocaust-surviving Jewish grandfather and my stepfather, Daniel Levin, whose body of work as a real estate developer and entrepreneur directly shaped my worldview on the power and possibility of entrepreneurship from my youth. (My stepfather’s walk around style management at The Habitat Company and East Bank Club directly impacted my view of building relationships when leading people.) I grew up inspired by their stories and role modeling. So I enrolled at Stanford Business School with the goal of becoming an entrepreneur. There, I was inspired by the great Joel Peterson’s extraordinary communication skills as a leader, values-based approach to life and management, and entrepreneurial leadership style and mindset, assets that continue to inspire me over the past 20 years that I have had the privilege of counting him as a mentor.
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?
I love too many autobiographies and biographies to count- the most profoundly impactful to me are probably Personal History by Katherine Graham and Einstein by Walter Isaacson, for the humanism they show behind the brilliance and courage in these protagonists. In addition, it’s no secret that I’m a massive Ayn Rand fan, and the book that I love more than almost any book I’ve ever read by her is Atlas Shrugged. The inherent tension between a rugged individualist and the compassion required to one’s fellow human beings and sense of civic duty are present in stark contrast by Rand, and intellectually, I wrestle with these competing values and beliefs to present. As such, that’s probably the book that has 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 former chairman of JetBlue, whom I talked about in my book, Leadership & Life Hacks under Life Hack #65: You’re not seeking daily balance. You’re striving for episodic balance. Here’s what “episodic balance” means to me: there are going to be times where 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, or we’ll spend a week to ten days visiting friends around the country or across 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 focus and shore up the key stakeholders in my life that are my husband, Hal Morris, and our children, Audrey and Henriette.
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 any given week), when I’m on the road, I’m always checking in with Facetime and texts, getting updates 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, after-school activities, grandparent support, 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!)
But the concept of Episodic Balance is that you cannot be everything to everyone every day. In fact, the only responsibility each of us has is to “put our own oxygen mask on first” (another hack) and make sure we are shored up for a successful day.
Instead, I think about achieving balance in stakeholder management over a series of days and weeks. If we widen the aperture of time to achieve “balance” over this larger window, it is achievable. Some days, I can nail being a kickass CEO and a great lecturer. Some days, a great mom and a great wife. Some days, a great sister/daughter/best friend, and a great board member. You get the gist.
To me, the key is being ruthlessly honest with oneself on who those stakeholders are (and are not), and ruthlessly prioritizing the effort and focus spent on them. While you cannot be everything to everyone in a given day, if you are highly focused, ideally you can “nail” two stakeholders in a given day and achieve balance of all stakeholders over a series of days or weeks. Not easy, but more achievable than “daily balance.”
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 working as a 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 happens to be around early childhood education at this chapter of my life, culminating in my current elected service on our local school board.
According to this report, only about 31.7% of top executive positions across industries are held by women. This reflects great historical progress, but it also shows that more work still has to be done to empower women. In your opinion and experience what is currently holding back women from leadership and management?
If we take a leap of faith that women are as talented and capable as men at leading companies, then you have to look at the ways in which women are brought into the leadership pipeline and the circumstances in which women are given the opportunity to lead. In general, I agree with Geena Davis, “If you can see it, you can be it.” There have been countless movements and efforts (especially in the last several years) to showcase female leadership, whether within a company, in media narratives, or in educational settings. As women are exposed to these examples, I am hopeful that these examples will inspire women to keep striving, keep climbing, and keep leading at the highest of levels, in corporate America and on corporate boards.
I am aware of the “glass cliff” phenomena — the concern that female leaders are disproportionately placed in leadership roles during times of crisis, and may thus be set up to fail — which I’ve experienced firsthand, albeit eyes-wide-open, when I was brought in as a turnaround CEO at Surgical Solutions. But walking into something highly challenging does not mean that you are necessarily set up for failure vs. success. The principles of what is needed to successfully lead through a time of crisis are truly timeless: clarity of mission, vision, and purpose; the ability to rally and align key stakeholders on mission and vision and operating values; and the ability to communicate those goals internally and externally to the marketplace. If you are authentic and a woman doing that, you’re going to do a great job. If you’re a strong communicator and a woman, you’re going to do a great job. If you’re a great listener and a woman, you’re going to do a great job. And if you’re engaging with stakeholders authentically and honestly, and as human beings (not people to be managed out or in), I do think those can be stereotypically feminine qualities that can be advantageous in a time of crisis. There’s something to be said for owning those qualities as determinants of success rather than potential pitfalls in male-dominated industries and roles.
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 leaders and managers?
One of the key attractions to me of the CEO role at Empower is the opportunity to acquire companies founded and led by women entrepreneurs. Our target seller is a 45–65 year old woman, who deeply values clinical excellence, the training of excellence in her team, and deliver of it to her clinic’s patients. It is both fun and gratifying to shepherd these women stakeholders through the sale process, inspiring them to join a platform that espouses their shared vision for the category.
Can you please share “5 Things We Need To Increase Women’s Engagement in Leadership and Management?”
- Teaching the how-to’s of entrepreneurship and leadership more readily in undergraduate and graduate education is important.
I walk the walk here by teaching at top business schools annually.
2. If you’re already in a leadership position, install qualified women in your organization.
3. “Demand” (Strongly Recommend/Request) Gender Equity on the Boards You Serve and in the Teams you Lead
When I became the CEO of Surgical Solutions, I walked in and unapologetically said, “I’ve run my own company for 10 years prior and there was gender equity on the board. We will need to appoint another woman to the board when I join for this to feel like a balanced environment in which to lead.” And the private equity firm listened and accommodated me.
4. Support flexible work environments.
I was a Silicon Valley CEO who dealt with four pregnant team members out of ten in a twelve-month period (one being me). Providing flexibility can be a major challenge to an organization, but I’ve found that women who are given flexibility are just as driven, resourceful, and dependable. If anything, they overshoot what’s required of them in gratitude for the flexibility they were afforded.
5. Be One, Get One: The Power of Mentorship
The more role modeling, the more sharing of entrepreneurial role models the way that Authority Magazine does to really continue to spotlight and highlight the promise of women as entrepreneurs and leaders will continue to make it more and more obvious that it’s a path women can pursue. In a place like Silicon Valley, I believe it’s “in the air;” 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 been founders and leaders before.
It’s never too soon (or too late!) to start being an entrepreneur.
Do things that can teach or showcase leadership and entrepreneurship on a very small scale. We try to do entrepreneurial things for our daughters who are 9 and 12. You know, make bracelets, sell bracelets. Bake cookies, sell them. And of course, lead by example.
In your opinion, what systemic changes are needed to facilitate more equitable access for women to leadership roles?
A couple things I’ve learned from McKinsey’s Women in the Workplace study are that women fall behind early in their careers, and that they are at a disadvantage in their daily interactions because they see fewer women around them. So, we need to support women getting promoted earlier in their careers and provide structures and environments that overtly support mentorship.
As a woman in a leadership position, I take a personal interest in students of mine at Stanford GSB or Booth who want to start and/or lead companies and help them in any way I can. My family and I are investors in a few seed-stage venture funds that invest in women and non-obvious founders like Ali Rosenthal’s Leadout Capital, or Jessica Yagan’s Impact Engine, that support the ecosystem of women entrepreneurs and investors. On a personal note, the only angel investing that I have done directly to date is in former students of mine from Stanford or Booth, and mostly in women-led companies. I try to walk the walk in my investing life, and I unequivocally ensure that our management teams walk the walk in terms of policies that address any gender pay gap and parental leave, which are in my direct span of control.
What strategies have you found most effective in mentoring and supporting other women to pursue leadership positions?
I have a whole chapter on mentorship in my book, Leadership & Life Hacks, and I’ve outlined the following hacks for mentors:
- Leadership Hack #48: Underscore that showing up matters. I am direct with ground rules and expectations for communication with mentees, and I’m clear about what I can realistically offer and commit to in regard to time and resources.
- Leadership Hack #49: Be an active listener. It’s tempting to jump in and solve things for mentees, but you have to hear them out first. They may not be asking you to solve anything, and although you might want to protect them from falling on their faces, sometimes the most valuable lesson you can teach them is how to bounce back from a setback.
- And finally, Leadership Hack #50: Do what you say you’re going to do. If I say I’m going to make an introduction or write a recommendation letter, I do it. Period.
How would you advise a woman leader about how to navigate the challenges of being a woman in a leadership role within a male-dominated industry?
For any person in a leadership role, but especially for a woman in a male-dominated industry, you need a network of people to back you. I turn to my mentors and colleagues/classmates/friends to gain advice from those who have navigated similar paths and can offer guidance both within the organization or industry and in general (male or female). I also expand my network by immersing myself in industry conferences and professional networks and by consuming the most respected industry publications; I make myself a sponge, surrounded by experts who often become informal or formal advisors with deep domain expertise. And in turn, I then look for fresh, smart, efficient PR opportunities to establish authority and leadership in my industry.
How do you balance the demand for authoritative leadership with the stereotypical expectations of female behavior in professional settings?
I’ve developed a style that is authentic to me, and I don’t necessarily think about it through the lens of balancing stereotypically feminine and masculine qualities. I employ the hacks in my book, like meeting people face-to-face whenever I can, taking care of my people, and getting to know people and make them feel valued as human beings. Inherent in that is a level of tailoring communication dynamics to people’s styles, being direct (yet always respectful), and being transparent. In my experience, this approach–even when news isn’t positive–instills confidence and builds trust. As I’ve already mentioned, perhaps that authentic and honest communication style might be stereotypically feminine, which is of course an advantage to women leaders who possess it.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
On a professional note, we hope to attract and partner with the very best women entrepreneurs in the medical aesthetics category. We want them to partner with us so they can focus on delivering clinical excellence and growing their enterprises, where we take on the “less fun” portions of running a MedSpa, e.g. marketing, technology. HR 101, finance, accounting, etc.
On a personal note, I may be borrowing this from Buddha, but I always say, if you want to learn, teach (Leadership Hack #19 in my book). I started a class at the University of Chicago’s Booth Business School entitled “Women as CEOs, Investors, Directors, and Executives.” It’s all about inspiring women to be leaders, whether of their own entity or someone else’s, and helping them connect with people who will help them achieve their goals as entrepreneurs. If I could start a movement to bring this kind of education to more women and girls in general, not just to graduate students at institutions like Booth and Stanford Business School, I hope to be one of many women leaders and lecturers to ignite a spark for the greater leadership and influence of women entrepreneurs and executives alike.
How can our readers further follow your work online?
AlyssaRapp.com where you can also sign up for my newsletter, #HacksTheNewsletter. Or, they can buy my book “Leadership & Life Hacks” on Amazon. 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.
About The Interviewer: Vanessa Ogle is a mom, entrepreneur, inventor, writer, and singer/songwriter. Vanessa’s talent in building world-class leadership teams focused on diversity, a culture of service, and innovation through inclusion allowed her to be one of the most acclaimed Latina CEO’s in the last 30 years. She collaborated with the world’s leading technology and content companies such as Netflix, Amazon, HBO, and Broadcom to bring innovative solutions to travelers and hotels around the world. Vanessa is the lead inventor on 120+ U.S. Patents. Accolades include: FAST 100, Entrepreneur 360 Best Companies, Inc. 500 and then another six times on the Inc. 5000. Vanessa was personally honored with Inc. 100 Female Founder’s Award, Ernst and Young’s Entrepreneur of the Year Award, and Enterprising Women of the Year among others. Vanessa now spends her time sharing stories to inspire and give hope through articles, speaking engagements and music. In her spare time she writes and plays music in the Amazon best selling new band HigherHill, teaches surfing clinics, trains dogs, and cheers on her children.
Please connect with Vanessa here on linkedin and subscribe to her newsletter Unplugged as well as follow her on Substack, Instagram, Facebook, and X and of course on her website VanessaOgle.
Alyssa Rapp On How We Can Increase Women’s Engagement in Leadership and Management was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.