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When I look back over the last 50 years, it feels like I have lived several lifetimes. Each one ended with a bold decision that turned my life in a new direction. I am about to make another one.

After 9.5 years at Pegasystems, I have decided to leave my corporate role and return to what I love most: building something from nothing. Something I am passionate about. Something that creates value in the market and in the lives I touch.

As of July 4th, 2026 (yes, Independence Day), I will be a free agent. A solopreneur with no salary, a lot of time, and complete freedom over how I spend it. That sounds exciting. It is also terrifying. I am choosing to step into uncertainty during one of the most disruptive moments in modern history.

I am going full founder mode. My corporate paycheck and equity are in the rearview mirror. My wife and I are selling our home and moving into an apartment so we can lower our expenses and give this next chapter the runway and focus it deserves.

This is not my first time betting on myself

From 2000 to 2016 I operated inside the Salesforce ecosystem, much of it as cofounder and CEO of one of the first Salesforce consulting firms. We built it, grew it, and sold it. I built wealth along the way. Then I lost all of it. A failed startup and a divorce reset me to zero.

In late 2016 I was doing some consulting and driving for Uber, trying to get back on my feet, supported by my girlfriend, a travel nurse who believed in me before I had much to show for it. She is now my wife. She and my parents showed up when things were hard, and I will never forget it.

What happened next is a big part of why I am building this company.

My stepfather introduced me to the VP of Alliances at Pega, who I quickly connected with by building trust and uniquely positioning myself. He saw a fit, connected me with several leaders to interview, and when he heard Pega was considering a corporate venture program, he put my name forward. A week later I flew to Boston to meet the head of corporate strategy. Thirty minutes in, he asked if I would meet the founder and CEO, Alan Trefler. A few days after an intense fifteen-minute conversation with Alan, I had an offer to build Pega's first corporate venture program.

A relationship got me to the table. From there, my own ability to quickly build trust with the decision makers and influencers I met, along with the experience I brought, earned the offer. That has been the quiet pattern behind every meaningful chapter of my career, and it is exactly what I want to help other people understand and use.

Gratitude

I am grateful to the entire Pega leadership team and to every colleague who supported my journey. I am especially grateful for the entrepreneurs I met through Pega Ventures, the clients I worked with through Launchpad.io, and the teams I was in the trenches with. The connections we built together created lasting impact for Pega, its partners, and its clients, and I am proud of what we did.

I came to Pega with a clear mission. Rebuild my career in a new arena. Create meaningful value for the company. Help entrepreneurs in the Pega ecosystem build their businesses and achieve their dreams. On a personal level, I wanted to get my two sons through the rest of private school, put them through college, and rebuild my life.

After I made the final tuition payment and watched my youngest graduate, I realized my "why" was complete. I had done what I set out to do. And in that space, a new fire started.

A framework I have used my whole career

That fire pointed me back to something I have leaned on for as long as I have been working.

My father, James Masciarelli, spent years helping startups through Fortune 1000 companies build strategic relationships through training and coaching. He called the approach PowerSkills. It is also the title of his book. When he retired, he transferred the entire body of work to me. For more than a decade I have wanted to update these timeless frameworks and make them work for a more connected, more technical world.

I am no master. But applying these skills, even at a basic level, is what helped me recruit and lead teams, bring out the best in people, raise funding, build partnerships, get deals done, and build a career worth being proud of.

Agentic AI made the timing clear. As AI reshapes nearly every industry, the real question is what stays uniquely human and valuable. I believe the answer is our ability to build trust, deliver value, and sustain genuine dialogue with the people who matter most. I call that Relationship Capital. It is an asset you can build, measure, and grow. And in the age of AI, it may be the most valuable asset a person, team, or company can own.

So I founded Power Skills LLC. The mission is simple. Help people and companies build the Relationship Capital that lets them thrive in the age of AI.

What I am building, in the open

I am doing this one step at a time, and I am inviting you to come along.

The newsletter you are reading. Every issue of Relationship Capital shares practical ideas for building trust and creating value with the people who matter most. Every issue includes a Value Deposit (a specific way to give value to an important connection) and a Trust Builder (a specific way to earn trust). When you subscribe, you will get my free Relationship Capital Workbook: a step-by-step guide to identify your most important relationships, set goals across your strategic, operational, and professional horizons, and score where each relationship stands today so you know exactly where to invest next.

A podcast, launching in late June. The Relationship Capitalists opens with an origin story interview with my father, James Masciarelli. From there I will sit down with AI startup founders, GTM leaders, investors, and the kind of superconnectors who live these skills every day.

Then a PowerSkills Mastery course, a community, and one-on-one coaching. And eventually an agentic platform for building Relationship Capital at MyVIPs.ai. (Go to MyVIPs.ai to join the early access waitlist.)

My goal is to help more than 100,000 people build the relationships that move their lives and careers forward.

This is the very beginning. I am going to be building in public, learning, sharing the wins and the stumbles, and getting more active online than I have ever been. I would be grateful for your honest feedback on how to make this genuinely useful to you.

Come along

The philosophy behind everything I am building is simple: invest in other people's success before you ask for anything in return.

So if any of this resonates, here is how to join me. Subscribe to the newsletter and grab the free workbook. And if you find something valuable here, share it with someone in your network. Consider it a value deposit into your key relationships.

Ideas for Building Your Relationship Capital Through Trust & Value in Every Newsletter

Value Deposit

Pick one person who helped you this year and tell them exactly what they did and why it mattered. Be specific. "Thanks for everything" is forgettable. "That introduction to X changed my year, and here is how" is unforgettable. Specific gratitude is one of the highest-return deposits you can make.

Trust Builder

Do one small thing you said you would do but have not gotten to yet. Send the link. Make the intro. Send the article. Small kept promises build trust faster than big ones ever could.

Thank you for being here at the start. It means more than you know.

With love and gratitude,

Jason

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