ENJOY THE WORK - Key Persons
Ever since I joined my first startup in 1996, I've enjoyed working with small, driven teams, helping to transform cutting edge technologies into real businesses. My first two startups revolutionized fiber-optic telecommunications, resulting in two acquisitions among the top 10 largest VC-backed M&A deals of all time. After the .com crash, I shifted my sights to consumer internet and started one of the world's first social networks, hi5.com, which grew to 60M MAU. Later in my career I followed the explosion of smart phones to found an app discover site that organically attracted 15M installs.
Beyond my life as an operator, I was an active investor and mentor including serving as President of Sand Hill Angels in Palo Alto, CA. I've long recognized that good advice and mentorship are both more rare and precious than capital. That led me in 2017 to join Enjoy The Work as a Managing Director and Partner.
I love the underdog. Throughout my career leading both early-stage, venture-backed startups and global private equity-backed corporations, I've been motivated to build teams that find creative, often unexpected paths to success.
My journey has taken me from an executive at AOL in the early days of the consumer internet to the management team of two venture-backed startups that successfully exited. I then joined the parent of the New York Stock Exchange as its first Chief Digital Officer. In the past decade, I was a private equity CEO at two different companies, both of which drove 9-figure revenue, and the most recent of which exited successfully in 2019. While a PE CEO, I concurrently founded a software business which we exited to a global travel business.
Over the past 25+ years, I have bought or sold dozens of companies and raised close to $1B in debt and equity. Through my career's work building executive teams at different companies, I discovered my passion for personal growth. I'm energized by helping others realize the best versions of themselves - particularly the underdogs - and I'm fortunate to do this with ambitious startup founders at Enjoy The Work.
I love the early stage journey, particularly uncovering the magical intersection between what the market wants and how to sell it. There are so many open questions, different stakeholders, shifting variables - it's like a game of chess where the right moves lead to rising revenues and happy customers.
I've had the good fortune of wearing many hats in my startup life from business development, to product management to sales. For the last 10+ years, I've built and led go-to-market teams for 3 organizations, Jive which went public in 2011, Origami Logic was acquired by Intuit, and TripActions, still a public company valued at over $5B at last check.
Building startups has fed my ambitions for years, and I joined Enjoy The Work so that I could impact not just one startup, but rather a portfolio of them across the globe.
I've spent the past decade advising CEO founders and their executive teams on leadership, strategy, growth, organization and culture, at companies ranging from Seed to Series D. My partners and founders range from first-timers to serial entrepreneurs self-funding their latest venture - and most share a common thread of purpose-driven intentions in both their business impact, and leadership aspiration. My work as an advisor and executive coach followed a decade and a half of CMO, go-to-market, and general management roles across both startups and new business/market development at Fortune 500 companies.
In nearly every advisory role, I hear the same question from founders: "Why does this have to be so hard?" Yet, every challenge is not a new one, and I believe deeply that when equipped with the right resources, relationships & know-how, founders would ask this question far less. And perhaps enjoy the work more.
Throughout my 20 year career, I've successfully built a $1B business segment for a large public company, guided the turnaround of a distressed $100M+ revenue business, launched and sold a venture-backed startup, and led a B2B SaaS business to global scale.
My first career was in hospitality, where I served as the first VP of Loyalty Marketing for Harrah's Entertainment and led the turnaround of a failing 3,000-employee hotel and casino company. In 2007, I founded my first startup, which I successfully sold after 4 years and several rounds of capital. Starting in 2012, I served as COO of Taulia, growing the business from seed to D in less than 3 years.
Since 2015, I have led Enjoy The Work, a firm of expert early stage operators who have combined their considerable skills to advise the next generation of startups to launch, grow and reach scale. I founded Enjoy The Work because I believed that the biggest positive impact I could have on the world would be to positively influence the next generation of startup entrepreneurs. I've dedicated my professional life to that end.
With 16+ years experience spanning management, sales and marketing, operations, and analytics, I've spent time working for nonprofits and for-profits, agency and in-house, Fortune 100s, and startups.
My career as a startup founder and product leader began after earning my PhD in Game Theory and Behavioral Economics from Caltech. In 2008, I founded my first startup, Crowdcast, and successfully exited the company in 2012. Following Crowdcast, I helped lead three more startups: Spigit (SVP Product), tenXer (Head of Product), and Swerve
After my four startup experiences, I ventured into the enterprise world and joined Salesforce (VP Product), where I helped ship the company's first AI product. But it was through my involvement in Salesforce's M&A process that I ultimately realized I wanted to return to startup life.
Each chapter of my career was chosen based off of where I'd find my next challenge. I'm a problem solver at heart, and I take pride in repackaging all that I've learned throughout my career in order to effectively mentor the next wave of passionate founders.
Over the last 20 years, I've founded and successfully exited three startups. First was Qloud, a B2C on-demand music streaming service that grew to over 10M monthly unique visitors. Next was Kapost, a B2B SaaS company that we grew to over $13M in revenue and 100+ employees. My most recent was Onward, a ride-sharing service for seniors that partnered with hospitals and medical facilities.
Alongside those experiences, I also experienced hyper-growth at Airbnb. From 2015 to 2019, I served as Head of Product for Airbnb for Work and Airbnb Luxe. While there, we grew our department's bookings from zero to over $1B in 2.5 years.
Although each company created value in different ways, I grew to appreciate the things that stay consistent. Building a high functioning team, shipping good product, honing a sales motion, raising capital, etc. Now I'm paying it forward as a General Partner at Enjoy The Work, grateful to work with founders bringing the next generation of technology to market.
While I've been involved with startups ever since founding my own software company in the mid 1990s, the bulk of my career has been defined by venture capital. In the early 2000s, I co-founded Pittsburgh-based VC firm, Birchmere Ventures.
Over the following 20+ years at Birchmere, we raised and invested six funds and our portfolio companies achieved a cumulative market valuation of $15 billion. Through those funds, I was fortunate to work with dozens of amazing entrepreneurs.
Throughout my career, my highest highs have come when lending a helping hand to well-deserving, high-achieving founders. My passion lies in watching others achieve success. Through Enjoy The Work, I am able to fulfill this passion by taking founder mentorship to a deeper level than I could in the VC world.
With more than 20 years as a technology product development and marketing executive, I've helped grow companies from seed stage to series F. I've led multiple companies through acquisition as a VP or CMO, and have worked with numerous CEOs to successfully raise $100M+ in funding.
Later, as I moved into consulting and advising, I sought to become an even better company advisor and leadership coach. I became certified with both the College of Executive Coaching and International Coaching Federation as part of this effort.
I believe in the importance of both hard skills and soft skills. I recommend tactical frameworks but help leaders find their own resourcefulness. I give specific advice regarding what to expect next quarter but believe an executive should always be improving their own intuition.
I love how Enjoy The Work allows me to help a much broader selection of companies achieve more every quarter.
I joined my first startup more than 25 years ago and was immediately delighted by the blank slate in front of me. I've always sought out companies that were early in their growth stories, which led me to join Amazon, Google, and Pinterest many years before they became some of the world's largest enterprises. The common denominator - novel software, products, and teams that surprised and delighted massive numbers of customers.
My joy comes from bringing new products to the world. I've learned that there is a right way, a harmonious way, to ship those solutions. And I'm grateful now to have the experience (and scars) to help others get there faster.
I've had a few careers in various industries, but independent of my functional roles, the most important skill I've mastered is the ability to ask good questions.
I've developed that skill over a 20 year career that has spanned banking, entrepreneurship, personal coaching and startup advising. I've helped start 6 businesses, including co-founding a software company that we built from start-up to a profitable multi-million-dollar global operation to a successful M&A exit.
I have my CPA license, multiple academic degrees and a professional coaching certification but above all else my greatest passions are mentoring my fellow entrepreneurs and volunteering at my kids' schools.