Lessons on Entrepreneurship (from Anthony Scaramucci)

Lessons on Entrepreneurship

Lessons on Entrepreneurship (from Anthony Scaramucci)

The skill and experience you amass in an area of professional competency is one thing. Taking that expertise and turning into a strong and successful business is another. In this blog, we review advice from media and finance mogul Anthony Scaramucci in his book “Hopping Over the Rabbit Hole: How Entrepreneurs Turn Failure into Success” and compare notes on our learnings over three plus years at DiligenceVault.

Be Bold

Boldness is clearly a key strength for Scaramucci and undoubtedly a reason for his outsized success in both finance and media. As a media mogul known for his conferences and his TV show, Scaramucci has great credibility to provide advice for how an entrepreneur can spread the word about their venture. His suggestions for success in this area include getting out and talking to the press, mounting a public relations strategy, using nontraditional marketing tools to get the message out, having killer customer relations, and focusing on what makes you different. Scaramucci asserts that ‘marketing takes courage.’
At DiligenceVault we are bold in terms of our vision for a vertically integrated SaaS technology to support the entire investment research and due diligence process. We could have targeted a narrow niche of the industry in which to build a business, but that only would have contributed to the tech Balkanization and integration frictions facing investors. Instead, DiligenceVault provides a comprehensive mutualized platform to take excess cost out of the industry.

Culture Matters

The values of Delegation, Empowerment and Accountability, as well as Creating an Ethical Culture are all well embedded in our Zeitgeist and topics that Scaramucci covers in his book. He espouses building a culture of communication, putting work into relationships, and encouraging the collaboration of business partners via generosity, leaving money on the table.

At DiligenceVault we share those values of personal empowerment and creating a community of colleagues we partner with and support, and who in turn partner with and support DiligenceVault. And our pricing philosophy leaves money on the table, as we seek to reward our business partners and our network for going down the path of long-term collaboration with us.

In addition to the above core values, given that DiligenceVault is a forward-thinking data and tech company, we add a component of Agility. This (along with our founder! 😉) drives us to keep up a brisk pace of excellence in innovation as well as client service, and ensures that our platform and our users are on the very leading edge of industry capability.

Build Relationships

Scaramucci shares effective networking tactics, like getting referrals and following up within 2 days to successfully build relationships. There are also the basic relational elements that Scaramucci calls the Triangle of Intimacy, which can only be developed over time: building trust, providing reciprocity, and leaving a trail of good karma.

At DiligenceVault, we are all about building relationships and paying forward! We have a tremendous network of clients and supporters in the industry who are energized about what they do and about leveraging technology to move the research process forward. They, in turn, support DiligenceVault by making introductions, giving us market color, and being references 😊. We look at people and enterprises in a holistic way. We communicate with and support our network, not just with tech but in any and all aspects of their roles and relationships.

Hopping Over the Rabbit Hole – Or: The Don’ts of Building a Business

Do’s: Entrepreneurs need to have a plan. It’s been commented, however, that the actual exercise of planning may be the most important part of the plan, because if you have thought through priorities and constraints, you are better able to respond to inevitable changes in the landscape and unanticipated challenges. The subtitle of the book – “Hopping Over the Rabbit Hole” – alludes to avoiding pitfalls that waste time, money, energy and relationships.

At DiligenceVault we have a roadmap, but it has been adjusted repeatedly. What has driven that? Client feedback and requests. There are a lot of people willing to share advice and a lot of good ideas out there. Which ones are we sure to listen to? Those that are shared in the form of requests or suggestions from clients, and those from people who have walked in our shoes. Often grand visions for our business are gratefully received and considered, and may hopefully be enacted one day – so keep the good ideas coming! But it is the clients and the active network who drive our priorities.

Don’ts: One very helpful Don’t from Scaramucci is: Don’t take anything personally. Much as any non-response or rejection may seem personal, the reality is that there are only so many hours in a day. Most people are focused on what they need to accomplish for their jobs and for the people they love – and we know they are likely encumbered by sub-standard tech! If someone doesn’t have time for you right now, you can’t take it personally. The best thing you can do is focus your time and energy on where you can add value now, and remain prepared to prove your worth in other arenas when the opportunity presents.


Scaramucci advises not overcomplicating your idea. At DiligenceVault, we also strive to keep things simple – we are the Common App for funds and allocators! We have found an unmet need and targeted it. As discussed in the book, we don’t reinvent the wheel at DiligenceVault; we adapt and improve it by leveraging digitization and automation.

Diligence (Yes, this is a Double Entendre!)

Scaramucci’s personal history of entrepreneurship and hard work mirrors that of other successful entrepreneurs. Like Warren Buffet, Scaramucci started his business career in boyhood with a paper route, which he strove to make the largest and most profitable one on Long Island. Scaramucci followed that with diligence in school and jobs at high-profile firms in the finance industry. There is no substitute for hard work, and a productive firm culture needs to place a premium on that. As Scaramucci puts it: “if you aren’t willing to put in the sweat equity, don’t expect any equity.”

Inspiration and Resilience

Inevitably there are challenges and setbacks that may seem daunting when your venture is growing and there is lots to do. How to ensure resilience, to be able to see around the corner so that you keep going in the face of seeming adversity? Scaramucci advises entrepreneurs to scout out the influencers, and in general to seek inspiration and to learn from the best and the bravest.

At DiligenceVault we find a lot of inspiration just about everywhere we look! As a data and tech company, we fully appreciate the endless supply of knowledge and information just waiting to be discovered, and we actively tap into the best and brightest thought leaders every day. The DiligenceVault platform has allowed us to engage with influencers who appreciate what we are building and who help us to move forward. From business and technical advisors, to academic researchers, we are building relationships with loyal supporters of our work. These relationships are a great source of inspiration, as we continually discover new ways that people create value and achieve success.

Why Read This Book & Write This Blog Now?

One year ago, the presidential pendulum swung in American politics, as it has every 8 years for the last quarter century. Whatever your views, the current administration has shaken up everything and caused everyone to reexamine their views and opinions with renewed vigor. Just two days after last year’s election, a very large custodian bank hosted a conversation with Scaramucci and their chief economist to debrief on the election and look at the path ahead. The bank also generously provided attendees with the book that Scaramucci had recently written, called “Hopping Over the Rabbit Hole: How Entrepreneurs Turn Failure into Success” – which did not get read at the time and took up residence on the shelf.

Anthony Scaramucci, however, has persisted in being one of the more engaging personalities to burst into the broader public consciousness over the past year – a fascinating character with an over-the-top personality and a name out of opera buffa. But he is also a wildly successful media and finance mogul. He was an outspoken supporter of the current President from early on, involved with many projects in the current administration, including a riveting, brief turn as White House Director of Communications. The recently announced launch of Scaramucci’s media company, the anniversary of the election, and the exciting growth trajectory of DiligenceVault encouraged a read of Scaramucci’s book.

What is striking about the author is his ability to be brutally honest in his self-reflection and in assessing his strengths and weaknesses. This is something that is much easier said than done, and likely key to Scaramucci’s success. He also comes off as surprisingly humble – with the occasional seeming humblebrag. It is undeniable that Scaramucci has been tremendously productive and successful, and with a personal toolkit that, like that of every other human being, has its limits. His advice is to believe you will succeed, as he clearly has through many ventures, and to use that strength to move forward. Scaramucci’s demonstrated ability to work past his weaknesses while leveraging his strengths, and his tremendous diligence, can serve as inspiration to us all. And we look forward to the success of his next act!

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