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Josh Feinblum of Stavvy: “Degree of authenticity”

As I tried to find the “5 things” I wish I knew 18 months ago, I realized that it’s not a question I can answer yet. Starting Stavvy has been a quest of trying to implement over 15 years of professional and personal learning. There are certainly things I would do differently if I were […]

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As I tried to find the “5 things” I wish I knew 18 months ago, I realized that it’s not a question I can answer yet. Starting Stavvy has been a quest of trying to implement over 15 years of professional and personal learning. There are certainly things I would do differently if I were starting over. However, I still feel like I’m another year or two from really being able to look back and understanding where things went wrong and what went right in a way where I could create a list like this with a degree of authenticity.


The COVID19 pandemic has disrupted all of our lives. But sometimes disruptions can be times of opportunity. Many people’s livelihoods have been hurt by the pandemic. But some saw this as an opportune time to take their lives in a new direction.

As a part of this series called “How I Was Able To Pivot To A New Exciting Opportunity Because Of The Pandemic”, I had the pleasure of interviewing Josh Feinblum.

Josh Feinblum is the co-founder of Stavvy, the remote notarization and mortgage facilitator, and a lifelong technologist with a focus on entrepreneurship, cybersecurity, privacy, and anti-fraud technology. Over the past fifteen years, Josh has been responsible for building and leading teams — from niche startups to large federal agencies — that have been tasked with tackling some of the largest fraud, abuse, and security challenges in the world. Josh also serves as a professional advisor at the Martin Trust Center for MIT Entrepreneurship, as well as venture partner at F-Prime Capital, where he evaluates and advises startups across multiple verticals.


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

My journey began on the rural Eastern Shore of Maryland, where my mother and father, a fourth-generation optometrist, launched their optometric practice — my first exposure to entrepreneurship. In the late ’80s, my parents purchased an Apple II clone — the Laser 128 — to facilitate this practice’s bookkeeping. While my two older brothers and I were fighting for computer time, no one knew in those moments how my access to that device would arguably be one of the most defining things that ever happened to me.

I spent much of my youth dealing with a few learning disabilities, including one called Dysgraphia. This disability made turning my thoughts into coherent handwritten statements very challenging, which may be why computers drew me in so quickly — almost immediately becoming a dominant part of my life. By the time I was ten, I had written my first lines of code.

Growing up in a time when my passion did not align with any school curriculum, the older I got, the less successful I was in school. Anything unrelated to technology couldn’t capture my interest, and I was falling academically behind. My parents, increasingly concerned, found an unsuspecting place that could bridge the gap between academics and technology; a small boarding school in northern Maryland called West Nottingham Academy.

I was lucky to find myself at a place like West Nottingham, which was impressively able to re-engage me academically and give me the structure to learn how to learn without suppressing my interest in computers. It was the first place I had ever been that had several other folks deeply interested in computers, like me. It was the first time I didn’t feel ‘out of place,’ and it gave me the confidence to continue formally pursuing how technology can change the world for good, and understanding how it can be exploited for evil.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

It’s hard to nail down a single quote that I would call my ‘favorite.’ I generally favor the theme that people should take risks, because it’s those risks that result in the most significant rewards. However, the individual quote that I think about the most comes from Eleanor Roosevelt: “In the long run, we shape our lives, and we shape ourselves. The process never ends until we die. And the choices we make are ultimately our own responsibility.”

Roosevelt played an active role in the suffrage movement and played a part in ratifying the long-overdue 19th amendment. It’s hard to compare anything I’ve been through to that journey, but I recall reading that quote in her book during a college assignment, as I was going through some personal trials and tribulations. For whatever reason, the message truly stuck — and it’s enabled me to fully embrace the notion that I can’t control everything around me, but I can control every choice I make. As a result, I spend more time worrying about things I can control, holding myself accountable for my current reality — and avoiding the placement of blame on others for situations I find myself in.

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

Brené Brown’s The Gifts of Imperfection was easily one of my most impactful reads. If you’ve read the book, you can probably see how it’s related to the quote above. To put simply, we are who we are. In the pursuit of happiness, we should be transparent and vulnerable. We should not feel shame in our history or our flaws.

For anyone looking to impact the world, lead people, or do great things — it starts with being honest with who you are, not blaming your past for where you are today or future transgressions, and surrounding yourself with people that respect you for you.

Let’s now shift to the main part of our discussion. Can you tell our readers about your career experience before the Pandemic began?

Much of my career had been focused on protecting individuals’ security and privacy by tackling large-scale technological, regulatory, and policy-related challenges. A few months before the COVID-19 illness began to emerge, I left my role as a Chief Security Officer at a large hosting provider and made my passion for entrepreneurship a full-time focus. My good friend and classmate Kosta Ligris and I joined forces to start Stavvy. We were committed to enabling lenders to more effectively and securely connect with the vendors they leverage during underwriting and settlement of real estate transactions while providing their customers with an integrated virtual closing platform.

What did you do to pivot as a result of the Pandemic?

Stavvy was in the process of launching our first product when the lockdowns began. Our prospective customers faced unprecedented operational challenges, dealing with record-high loan volumes while actively retooling to support a remote workforce.

We recognized that this dynamic would make it tough to sell our initial product. Still, we saw an emerging need for software solutions tailored towards emerging novel approaches to remote notarizations, especially in New England area states. We decided to repurpose some technology and delivered our ‘Remote Ink Notarization’ product in just a few weeks.

Given the demand for the product we had delivered, we also found ourselves in a position to hire some wonderful people that had endured a pretty traumatic round of layoffs at some of Boston’s most iconic technology companies. Given the accessibility of great talent, we accelerated our hiring, more than doubling our number of employees less than six weeks after the initial shutdowns.

Can you tell us about the specific “Aha moment” that gave you the idea to start this new path?

Our path forward was determined by a few weeks of discussions and observations. We knew we wanted to do something — and given the dire predictions this March, we were very much gearing our mindset towards how we could help. As we evaluated some of the emergency orders and legislation going around New York and the New England states, we started to hear about people conducting notarizations of some significant transactions over various consumer video communication tools. We knew these tools were insufficient to meet the regulatory requirements outlined in the emergency government actions and identified that we had technology we could deploy quickly to support this form of transaction.

How are things going with this new initiative?

It’s hard to imagine things could have fared better for us based on the twists and turns we’ve navigated. While we would never wish for a tragedy like this, we are grateful that we could contribute to society’s response while using it as a launching point for Stavvy. Our ability to deliver technology that could provide even a little bit of assistance by allowing people to complete complex financial transactions remotely is a true blessing. We’re equally grateful that successfully delivering that solution enabled us to help many of our fellow Bostonian tech-folk during the unexpectedly challenging times they found themselves facing.

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?

A gentleman by the name of Vince Watchorn changed my life. As my high-school advisor, he invested a lot of time in my development as a human. It’s tough to find a single story that encompasses all he did for me. Still, one of my favorite takeaways from the early stages of that relationship was the brilliance of spontaneity.

It wasn’t uncommon for Vince to come into a few of our rooms on a dreary Friday night after a long week and say ‘let’s go.’ In just a few minutes, we’d go from winding down from the week to being in his car beginning the 60-minute journey to Philadelphia ‘just’ to get a cheesesteak.Embracing how unpredictable events in our lives can be the most enjoyable has always stuck with me as a result.

Can you share the most interesting story that happened to you since you started in this new direction?
Starting a company provides for interesting stories every day. Stories of never-ending roadblocks, unexpected successes, and surprise failures — all hopefully accompanied by an undertone of optimism and perseverance. There is no single story during our pivot that stands out. All of those stories are overshadowed by the reality that I’ve found myself working to build a business, amidst a global pandemic, in one of the most unpredictable times in modern history.

What stands out to me the most is a ‘macro story’ about the relationship I have with my cofounder. Most people engaging with startups hear consistent stories of struggles between the founding team. Amongst the entropy we’re dealing with, the single biggest thing I reflect on is how my relationship with Kosta has morphed and continued to grow stronger every day. Being a founder is a lonely place. Having a partner-in-crime that I can rely on, grow with, and trust has made an incredible difference in my personal experience, and hopefully, the probable success of Stavvy.

What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

As I tried to find the “5 things” I wish I knew 18 months ago, I realized that it’s not a question I can answer yet. Starting Stavvy has been a quest of trying to implement over 15 years of professional and personal learning. There are certainly things I would do differently if I were starting over. However, I still feel like I’m another year or two from really being able to look back and understanding where things went wrong and what went right in a way where I could create a list like this with a degree of authenticity.

So many of us have become anxious from the dramatic jolts of the news cycle. Can you share the strategies that you have used to optimize your mental wellness during this stressful period?

Every day, I remind myself that social media and the broader media apparatus amplify the negative, and not just a little bit. From a quantitative perspective, we live in the most peaceful, prosperous, and promising time in the history of our race.

As our population booms, we’ve made huge strides reducing the number of humans living in extreme poverty, with the absolute numbers of people living under that dire line plummeting over the past two decades. Global child mortality is down by more than half since 1990, which isn’t just benefitting affluent nations. Child labor is declining, hunger is falling, and life expectancy is rising for everyone. Even if there is a slight short-term uptick, violent crime is near all-time lows after decades of decline. More people live with the freedoms of democratic institutions across the globe than ever before. People around the world are more educated, and thus global literacy is increasing. Renewable energy is getting cheaper, the internet is getting more accessible, and access to space travel is becoming more available. We’re even poised to deliver a vaccine to one of modern history’s most devastating pandemics in under a year, beating the fastest vaccine delivery in history by three years.

While there is still enormous work to do, our level of progress on critical societal and technological issues is extraordinary over the last 20 years and only accelerating. We should be driven and excited by our current progress and the opportunity for future advancement. People or resources that make you feel bad about our progress, as opposed to enabled to continue that journey for humanity, should be tuned out — they exploit how our brains work and add no value.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I would want to focus on unlocking the power of human positivity. People should be able to disagree and remain in close relationships. We should be resistant to the onslaught of data that exploits our psychological biases to put us at odds with each other and feeling exhausted about the current state of society — even though, as mentioned above, it’s quantitatively the best it’s ever been.

Work together, support each other, and continue to make the world a better place — without the divisiveness we’ve rationalized as ‘acceptable’ for whatever reason.

Is there a person in the world whom you would love to have lunch with, and why? Maybe we can tag them and see what happens!

This one is simple: Satya Nadella. What Satya did at Microsoft is extraordinary. He took one of the most iconic tech companies in the history of the world, that was on the brink of relative collapse, and made it one of the most desirable tech brands again. He made bold and fundamental changes, big bets, and made Microsoft not only a place where the best and the brightest wanted to work again, but positioned Microsoft to lead some of the most important innovations currently being worked on.

How can our readers follow you online?

I’ve not been nearly as active on social media as I used to be, a trend that I suspect will change over time. People can find me on Twitter, Instagram, and Linkedin @jfeinblum.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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