I recently had the opportunity to sit down with my good friend, former boss (from way back!), and fellow Boston entrepreneur, Jeff Glass. 

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While Jeff’s accomplishments and awards are too numerous to list, here’s a summary: a serial entrepreneur, Jeff is currently the co-founder and CEO of Hometap, which was recently recognized as one of America’s fastest growing companies. Before founding Hometap, Jeff was a managing director at Bain Capital, and has built several successful companies since the age of 22. 

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Hometap helps American homeowners by providing an innovative, debt-free way to access their home equity. Jeff has received numerous accolades for his current leadership and the culture at Hometap. E&Y has selected Jeff as CEO of the year twice. 

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On a personal level, Jeff is full of wisdom, perspective, and good humor (most of the time!). We touched on several topics during our conversation, including Jeff’s leadership experience, and how a founder/CEO needs to think about their on-going role. We also explored our shared views on accountability and what motivates Jeff to keep building companies.

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Identify what fuels your entrepreneurial mindset

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Jeff ignited his entrepreneurial career at age 17, going door-to-door selling office furniture to make money for college. In college, he started a clothing and memorabilia business to help pay the bills. “My freshman year, I couldn't afford a college sweatshirt — I was a financial aid student and was totally strapped for cash,” Jeff says. “My roommate and I were so outraged by the markups that we decided to create a business selling college clothing for a more affordable price.” 

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One of Jeff’s early role models was his father, who was an entrepreneur out of necessity. “In a lot of ways, I'm what Dan Glass would have been if he’d had the opportunities I've been afforded,” he says. A high-school dropout, Jeff’s dad struggled to land a salaried position, which led him to work a series of commission-based sales jobs. Finding customers was a survival tactic — his income was exclusively tied to his performance.

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Talking to Jeff, it's clear that seeing his father hustle out of necessity has been a driving force that fuels him, even to this day. “My dad felt like he had control over his career, for better or for worse. That’s where much of my entrepreneurial drive comes from,” Jeff says. 

‍Key takeaway: Work experience does play a large role in shaping CEOs and founders. But early role models and events play an equally influential role in driving great entrepreneurs forward.

“Absurd” ideas might be a good thing

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Now that Hometap is successful, it has become known as an innovative game-changer. But it didn’t start that way. 

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“Everyone told us this was the dumbest idea ever,” Jeff says, reflecting on the early days. 

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The insight for Hometap came from a conversation with Jeff’s colleague — now a co-founder — about how home ownership is unattainable for many. Jeff had also heard about someone who had sold his home to free up capital to pay for his mother-in-law's healthcare. This led him to think about how homeowners need more equity alternatives. The only alternative at the time for a homeowner was to borrow and borrow more.

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Jeff had previously started companies that had benefited from investment through venture and equity capital. That’s when the light bulb went on. “Why can't we give a homeowner a similar option?” Jeff thought. His team started conversations with homeowners, who were enthusiastic about the concept. However, it was a different story with the lending industry, capital markets, and the real estate world. Jeff and his team faced a lot of initial skepticism from this segment about whether homeowners and investors would buy into their idea. But then Hometap proved them wrong. “When everybody in an industry is telling you that your idea is absurd, you know that one of two things is true: your idea is really absurd or you’re onto something really smart,” Jeff muses.

‍Key takeaway: Have conviction in your vision even if others don’t agree. But be relentlessly curious and honest with the feedback you receive during a comprehensive customer discovery process. Find a burning pain point and attack it!

Relationships and mission are everything

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When I asked Jeff what he values most about his career, he landed on two things: relationships and mission. “When I look back over all these years, what I cherish most are the relationships I’ve built,” Jeff said. “That’s what entrepreneurship gives you — building a team, raising capital, talking with customers, meeting people at events and conferences. You build relationships.”

Many of Jeff’s most important friendships and relationships are a result of his professional career. He finds value in building and maintaining long-term relationships instead of focusing on fleeting or transactional interactions.

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Hometap’s mission is to make home ownership less stressful and more accessible — which motivates Jeff to wake up every day. When he started his career, he didn’t realize how a sense of mission could drive him. A focus on his mission motivates him to do more than just build a good business. “We're on this planet once, and we want to feel like we've moved something forward in a positive way,” he says. 

‍Key takeaway: It is the people that make the journey worth it. Venture funding, seven-figure deals, and large exits all pale in comparison to the relationships that you build along the way.

Don’t be afraid to lose your job

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Founders should cultivate humility about their strengths and weaknesses, especially as their business scales. Jeff believes that founders should not be primarily concerned with preserving their role. As he puts it, “If you're a good founder, all you should be thinking about is, how do I help to build a great company and how do I make this successful for everybody?” 

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If it is in the company’s best interest for someone else to be the CEO, then founders should be the first to get out of the way. Jeff realizes that this is easier said than done. But it is possible if founders take the long view and focus their time on energy on creating a great company. 

‍Key takeaway: Founders should be open to change, but not fear it. Roles and responsibilities inevitably need to mature, change, and grow over time. Sometimes that works for a founder, and sometimes it doesn’t.

Accountability is critical for leadership and team-building

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A recurring theme in my conversation with Jeff was ‌the importance of accountability. It is perhaps the most defining characteristic of a successful start-up leader.  This is one of the key traits I look for in the founders that I invest in at Unusual Ventures. At my previous company, SessionM, I created a quarterly shoutout called the PACT award. It stood for Purpose, Accountability, Commitment, and Teamwork. While all these traits matter, accountability was a key focus for me — it creates the conditions for success within a growing company.

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As a leader, Jeff deeply feels the need for accountability. He will fight relentlessly for all his business stakeholders, including his team and his customers, because they have placed their trust in him. This responsibility is not easy and comes with a cost — it can be incredibly stressful when you know you have to deliver for all the people involved with your business. But as Jeff puts it: “You owe it (to your team) to do everything possible to ensure success and help build their careers, lives, and professional skills. That’s your job.” 

‍Key takeaway: While it is not easy, accountability should be something that you thrive on as a founder and it should drive you everyday to do your best.