Meet Nanigans Co-founder & CEO Ric Calvillo, hear lessons learned from the ups and the downs of the startup journey, and data-driven insight about what most Facebook advertisers are getting wrong.

My guest the week is healthcare VC superstar Michelle Dipp. Dr. Dipp is a co-founder and Partner of Longwood Fund, having co-founded Longwood portfolio companies Axial Biotherapeutics and OvaScience, both of which she now serves as Chairman of the Board. She previously served as the CEO of Alnara Pharmaceuticals (acquired by Eli Lilly), Verastem (NASDAQ: VSTM) and FlexPharma (NASDAQ: FLKS). BOTH of which

Michelle Dipp is an overachiever in an industry of overachievers. As a young girl growing up in El Paso Texas, though, she dreamed of being a professional ballerina. She worked diligently at it for 8 years — studying under a Balanchine dancer from age 4 — before two attempts at New York auditions ended in heartbreak. Six years of strict Catholic school later, she failed again… this time to get into Harvard, which had become her “dream school” after coming to terms with her mother’s loving but pragmatic advice on ballet and on life. “Sometimes no matter how hard you work,” she said, “you’re just not going to be good enough. And you need to get over it.”

Near as I can tell, Michelle Dipp was never not good enough for anything again. Her Oxford undergrad experience turned into 12 years of study abroad, culminating in a stint as a first class medical researcher. Her work, energy, and leadership skills garnered first the attention and then the high regard of both Big Pharma and Big Private Equity. Driven to the cutting edge of medical science, she used her power and influence to develop promising new platforms into a series of companies that would make any VC salivate. In her spare time she helped build the venture capital firm that would spawn them all — Longwood Fund — whose mission “to identify technologies and found companies that will advance new therapeutics that not only make a difference in the lives of patients worldwide, but also create significant value for investors.”

Michelle Dipp wants it all. She wants what her mom had, which as a nurse in a Texas border town was to make a difference in the lives of real people across a broad spectrum of cultural and socioeconomic circumstances. And she wants what her dad had too, which is to build and lead businesses that make a difference in the community of which they are a part.

That’s what Michelle Dipp wants. And there is simply no doubt she is good enough to get it.

In our second segment this week Michelle and I talked about the differences, similarities, and inevitable convergence of the two great tribes of the Boston innovation ecosystem, Healthcare and Tech. Using the example of her latest project — Axial Biotheraputics — Michelle explains how new treatment “platforms” come about on the healthcare side, and the process by which enterprising entrepreneurs turn promising scientific breakthroughs into therapies that help people in the real world.

Michelle is obviously a rock star, but also a delight to spend time with. I think you’re really going to enjoy getting to know her, in particular the person behind the pedigree.

My guest the week is venture capitalist and charter G20 Member Jeff McCarthy. Jeff’s a Partner at North Bridge Venture Partners, focused mainly on materials. He played leadership roles at two early, successful companies within the North Bridge portfolio, Cadia Networks and New Oak Communications, where he was the CEO until that company was acquired by Nortel. Before joining New Oak, Jeff was Vice President of sales and business development at Cadia Networks, a developer of ATM concentrator products for the service provider marketplace, and held senior management positions at Wellfleet Communications, including Vice President of Carrier and Channel Operations. Jeff is a proud and active graduate of the Northeastern University School of Management, and serves as an advisor to the University.

In this week’s second segment Jeff and will focus on a problem that seems like a great one until you have it, which is how to pick the right VC partner when you have more than one to choose from. Jeff will share thoughts on the importance of chemistry and vertical expertise, respond to my question about what’s different for female entrepreneurs, and compare funds specialized in individual stages of the venture journey with those that invest throughout it.

As always, How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.

Here now, my conversation with G20 Member Jeff McCarthy...

Hello and welcome to a very special episode of "How Hard Can It Be"...Up close and personal with the real people behind the hits and misses in Boston's venture capital ​big time.

My name is Bob Hower and I'm the Co-founder of G20 Ventures. You can​ ​​​follow me on Twitter at @bobthevc, and​ link to our Medium publication at G20vc.com.

​Each week we'll​ ​be ​getting​ to know one of the​ ​luminaries in our local startup community, and drill into a specific area of their​​ ​expertise for the benefit of other entrepreneurs and investors.​

My guest the week is the usual host of this podcast, my new partner Mike Troiano! Mike is a new venture capitalist who brings nearly 25 years of executive leadership and marketing experience to bear for entrepreneurs. He most recently served as the Chief Marketing Officer of Actifio, a global enterprise data-as-a-service provider he helped turn from an obscure virtualization technology into a venture capital "unicorn" valued at over $1.2 Billion. As CMO from 2012 to 2017, Mike helped grow revenue over 80% per year, creating the Copy Data Virtualization category while expanding the business into blue chip accounts across 37 countries.

He spent his early career at top worldwide ad agencies including McCann-Erickson and FCB, and was named the founding CEO of Ogilvy & Mather Interactive in 1995. He later served as the president of NASDAQ-listed systems integrator Primix, and as General Manager of mobile content pioneer m-Qube from inception through one of the largest Boston-based venture capital exits of 2006.

In this week’s second segment Mike and I talked about the importance of belonging, what makes him such an effective communicator, how he decided to become a VC and what it means to him to be a great one. We also discussed what all great entrepreneurs have in common with bruce Springsteen, something this Garden State native liked a lot.

As always, How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.

My guest this week is ezCater Co-Founder and CEO Stefania Mallett. Stefania has spent over 25 years building and growing technology-enabled companies that solve real business problems. She co-founded and successfully sold InSite Marketing Technology to what is now KANA on NASDAQ, and prior to that led National Logistics Management (a broker for $225M in transportation services) to profitability for the first time in 4 years. As the COO of IntraNet (now ACI Worldwide,) Stefania revamped the firm and vaulted it to #1 in its market, a position it has maintained for 15+ years.

What I find remarkable about Stefania is not only the depth of her competence but the breadth of her interests. A self-proclaimed “systems thinker” and engineer, she emerged from a difficult and non-traditional childhood determined to make sense of the world, proceeding through a hugely successful and entrepreneurial career to do exactly that through a series of executive management roles across a dizzying array of industries and company types. Far from the overly-intellectual engineer stereotype, though, she’s managed to remain a warm and insightful person who clearly cares deeply for the people she’s working with the build ezCater, a neat little company which itself has a story worth telling. We’ll spend our second segment doing just that, walking step by step through the unexpected yet highly typical twists and turns that characterized ezCater’s beginning, through the disciplined approach to management that’s created one of Boston’s most successful and thriving marketplace businesses.

How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.

My guest this week is Patrick Sweeney, an Olympic athlete turned technology entrepreneur turned full time adventurer. Patrick chases adventure for a living, propelled by a passion to help others do the same through corporate speaking engagements and network television appearances, plus an upcoming book in 2017.

Patrick grew up a working class Irish kid outside of Boston, and was shaped by a dramatic life experience he’ll share in our talk. He finished 2nd in the 1996 Olympic trials rowing the single scull and won international races from Canada to Norway. After attending a top business school, he built multiple ground-breaking technology companies, earned six patents, wrote two award winning books and appeared on media outlets from CNN to Bloomberg, CNBC, and The New York Times.

One day, though, while working the 80-hour weeks and living the intense life of an entrepreneurial leader, Patrick got a wake-up call in the form of a life-threatening illness. When he recovered, he took his first steps toward finding his own adventurer again, unlocking a passion and energy for life all too often lost in the pursuit of material wealth. Today Patrick’s focus is on breaking world records and embracing every day as if it were his last. In Feb 2015 he became the first person to bike to Everest Base Camp in Nepal, and has now become the first to attempt cycling the Seven Summits. His mission is to help millions around the world find their adventurer within, and our second segment today focuses on the process of overcoming fear that’s central to achieving that or any goal in life and in business.

This conversation is a fascinating one about breaking through what he calls the “fear frontier,” covering ground from startups to parenting, the limiting functions of our lizard brains, and the journey to find the “genius” we all have at the intersection of our passion and our vocation.

PLEASE take a minute to subscribe to this podcast on iTunes, Overcast, or Pocket Casts, and consider giving us a quick, 5-star review on iTunes. It really helps spread the word and I would sincerely and personally appreciate it.

How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.

After 20 episodes of the HHCIB Pod, it's time to ask... well... how hard it actually is?

How are we doing? What could we do better? We've set up a quick typeform here to gather up your feedback, would love to hear from YOU what we're doing right and how we could do it better.

So let us know: https://miketrap.typeform.com/to/YEeSzu

My guest this week is Matt Johnston, Chief Executive Officer of Mautic, the leader in open source marketing automation. Mautic makes it easy for you to put the right message in front of the right person at the right time, empowering enterprises and agencies with a flexible, open platform built for us by us. Before joining Mautic earlier this year Matt was the Chief Marketing and Strategy Officer at Applause (formerly known as uTest). An integral part of Applause’s growth after joining in late 2008, Matt led that company’s marketing, community management, partner channel, and company strategy, helping it become one of Boston’s most highly regarded enterprise technology players. Before that he played a range of senior and strategic marketing roles at OnForce, Mimeo, and Herman Miller office furniture.

Our second segment this week is a real treat for anyone interested in what it means to be a Chief Marketing Officer in 2017. Matt and I together have held just about every marketing role you can have, including the one at the top, and our conversation covered everything from the anxiety and stress of keeping up with the latest technology phenom du jour to the roots, current reality, and future of the latest and greatest Account Based Marketing (ABM) model. It’s always fun to trade war stories with another senior marketing guy, and you’ll be a fly on the wall for a conversation I know we both really enjoyed.

How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.

My guest this week is Pierre-Loic Assayag, the CEO and co-founder of Traackr, the world’s most powerful and effective influencer management platform. Traackr lets marketers scale their influencer marketing programs by focusing on the individual people with the greatest impact on their objectives. Their customers include Coca-Cola, HP, OpenTable, Capital One, Kiehls, Travelocity, SAP and Adidas. Half of the top 50 communications agencies today use Traackr to drive successful social programs and earn more attention by engaging with the right people, an amazing achievement for a company just in the process of raising its first round of institutional capital.

A longtime mar-tech veteran, Pierre-Loic has deep expertise in advertising and marketing innovation across the digital space. After starting his career at P&G, Pierre-Loic became Peugeot-Citroen’s first Director of New Media heading up an international portfolio of information technology projects. He went on to join the frontlines of the Internet economy at places including Viant and Optaros, bringing blue chip customers the vision and execution they needed to survive and thrive in a media landscape transformed by the slow, painful death of traditional mass media.

In our second segment we’ll talk about a subject near and dear to any entrepreneur’s heart, which is when to raise money. Traackr’s been remarkably capital efficient in the way it’s grown into a global company, and that’s because Pierre-Loic has some strong views on the relative importance of customer revenue and investor capital. He also has a very specific and I think pretty unique way of thinking about when to go raise money, a model based on aligning your interests with that of investors I think could save a lot of us a lot of heartache as we journey down the road.

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How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.

My guest this week is Eric Paley, Managing Partner of Founder Collective, an early stage fund begun by a team of entrepreneurs who themselves launched companies and led them through successful exits. Founder Collective is focused on helping the next generation of great entrepreneurs build important and lasting businesses through it’s refreshingly clear and often-stated mission, to be the most aligned fund for founders at the seed stage. Previously, Eric was the CEO and co-founder of Brontes, which was acquired by 3M in 2006.

Founder Collective’s prescient investments in companies including Pill Pack, Seat Geek, the Trade Desk, Periscope, Buzz Feed, Hotel Tonight, and Uber have made it one of the most prominent seed stage funds in Boston and beyond. Fortune magazine’s influential Term Sheet recently identified Founder Collective as among a group of VC firms outside Silicon Valley who were moving investors beyond their strict belief in "the best and the rest" in venture, matching or beating the performance of the handful of storied West Coast firms to deliver some of the best performing funds of the past decade from firms that didn’t exist before the dot-com bubble.

Our conversation on the importance of “founder friendliness” included Eric’s perspective on the challenges facing portfolio star Uber right now, an exchange I think our regular listeners will find particularly interesting.

In our second segment Eric and I turned to what he calls The Idea Myth, the belief that every great company finds its genesis in some flash of inspiration born in the mind of some genius entrepreneur. The reality, and the core investment thesis of Eric’s firm, is that venture success tends to emerge from teams who deeply understand customer value creation, who have the talent and the will to persist in solving the the seemingly endless string of mundane challenges that must be overcome to will a successful company into existence from nothing. It’s a refreshing reminder of the importance of execution in a business that too often elevatea strategy above all else, and a view I very much share with him and his partners.

How Hard Can It Be is sponsored by G20 Ventures, early traction capital for East Coast enterprise tech startups, backed by the power and expertise of 20 ​of the Northeast's most accomplished ​entrepreneurs. G20 Ventures.​..​​ ​People first.

How Hard Can It Be is ​also ​sponsored by Actifio​, the world’s leading Enterprise Data-as-a-Service platform. Deliver your data just like your applications and infrastructure... as a service available instantly, anywhere. For hybrid cloud, faster DevOps, and better business resiliency, Actifio is Radically Simple.