Dean Walsh has traveled across ecosystems and hierarchies as a bridge between eras, one of the last paperboys, who rode his bike and mind on a path from neighborhood streets into the world of high growth startups. Today, he serves as the Senior Program Manager for TiE ScaleUp, an equity free accelerator program for Boston-based seed startups.
Dean started working at seven years old, delivering newspapers around the North Shore. The daily route was an influential part of his childhood, a type of mini-entrepreneurship that required him to sign new subscribers, manage billings, and practice customer service.
At home, Dean was surrounded by electronics (he received a volt meter for his fifth birthday). His dad was an electrical engineer, working for GE for more than 40 years, and was on the road for months at a time. When he was home, they built RC cars, instruments, models, and classic analog electronics. His mother, a special needs teacher, supported his inquisitive nature and encouraged him to try his best in school. Through a series of twists and turns, his paper route helped earn him a scholarship to Phillips Exeter, where he lived and learned with brilliant peers, students from all sorts of different backgrounds & cultures across the world.
After high school, Dean attended NYU but later transferred to the University of Rochester. In between, he went to woodworking school and considered a career in the trades. But the scholarship Rochester offered him was too good of an opportunity to pass up.
Dean spent his undergrad years preparing for law school, and jumped into a firm right after graduation. But after just a month chained to a desk filling and filing documents, he knew. The legal profession wasn’t for Dean.
So he took a walk. Like, a really long walk. Dean moved back home to work at a local apple orchard to save a few bucks before he set off to hike the Appalachian Trail for the summer. 2,200 miles of thinking will help a person find clarity. From April to September, he walked.
Dean reflects back on that summer fondly. Having the opportunity to walk and think about what he wanted to do with his life allowed him plenty of time and space for reflection in between conversations on front porches with locals from Georgia to Maine.
When he returned home, he moved to Boston to join Justice Resource Institute, a local social justice nonprofit. They had a Public Health division with a mandate to help Americans live healthier lives. The organization helped combat injection drug use and homelessness, support local LGBTQ youth, and much more. In an Operations & Project Management role, Dean worked cross functionally across a team of 100 people, with various projects & initiatives.
He had been in the role only 6 months when the pandemic struck. With his apartment right down the street from their offices, Dean sprang into action. He helped keep a dozen programs operating, delivered laptops by bicycle (with prior experience in the role) to students in need, and distributed hundreds of thousands of dollars in direct aid to members of the community. It was a poignant time and role with so many housing and food insecure people looking for help. With the needs and mission of the organization evolving, priorities and budgets shifted so Dean set out to find a new home.
He had also been applying to PhD programs but, when that path didn’t quite pan out, Dean started looking for a new adventure. While networking he met Laura Teicher, the President & Executive Director at Forge, the sister non-profit to Greentown Labs focused on sustainable manufacturing. Laura had previously been the Executive Director of TiE Boston and helped make him aware they were looking for a new Program Manager.
TiE Boston is a membership organization of entrepreneurs, executives, and senior professionals of Indian origin focused on fostering future innovation. They were looking for someone to manage their TiE ScaleUp Accelerator program in Boston and, for Dean, it was a really cool opportunity to jump into tech while seeing a bunch of different aspects of building startups.
Boston is one of TiE’s largest worldwide chapters and Dean was excited to ramp up with mentorship from Neeraj Chandra, an accomplished executive, board member, investor, and leader who had previously worked in worldwide strategy for IBM. Neeraj tragically passed away in his mid 60’s just a week into Dean’s tenure while on a trip to visit his son.
Not only was Dean new to startups and the technology industry but the leader who he was due to learn from was no longer there. It was a difficult situation for everyone. Dean had to jump into the fray and get up to speed by talking to dozens of entrepreneurs and investors, and reading everything he could – “4 Steps to the Epiphany”, “The Lean Startup”, “Mastering the VC Game”, “The Power Law”, and many more. The context was helpful but so was learning the vernacular.
He set out to recruit startups for their upcoming accelerator program, talking to dozens of founders and learning to ask the right questions to become an informed, conscientious evaluator. Dean quickly figured out how to zero in on what early stage startups were building and how they were doing it to help find the perfect candidates whose businesses they could help accelerate.
Second, he had to go run and execute the actual program. After recruiting a 15 company cohort during the peak of the market (Nov ‘21), he has continued to support those companies and teams through the program as conditions have tightened.
Leaning on the curriculum TiE had already built and bringing in additional speakers & mentors, attending the program himself helped Dean continue to get up to speed. He learned about GTM, R&D, and everything else he needed to learn to jump in and help their various companies.
TiE ScaleUp is in the midst of its 10th cohort and Dean has now run the program three times. He’s iterating on the program design and continuing to build relationships and grow the alumni resources too. Dean continues to support seed stage companies through TiE and aspires to work with more TiE chapters across the world, especially in India bridging learnings from both cultures from his seat in Boston at one of the oldest & biggest chapters. He’s continuing to meet with talented founders and connect them to TiE’s amazing resources of accomplished entrepreneurs & executives.
Dean has also been working to evolve his mindset over the past 12-18 months. After the loss of his boss just a week on the job, he experienced the loss of his father a year later. TiE was very supportive, and these personal & professional experiences have prompted him to reflect on his life, career, and his overall priorities in life. With all that he has experienced, he tries to live in the moment and take advantage of what comes across his path. Opportunities arise and you have to be ready to grab onto them when they come with a focus on adaptability and resilience. Dean continues to seek balance to go the distance over the long term, checking in on himself along the journey.
Getting at the Heart of the Company
Dean meets with a lot of startups regularly. Hearing from all sorts of different founders & teams at different phases of their journey has helped him work with founders to get to the heart of what entrepreneurs are trying to accomplish.
One of the things he has worked hard at, in partnership with TiE companies, is to pursue a line of questioning that helps both parties reword their positioning in order to get clear on their mission.
Dean often works with founders who have decades of specialized knowledge who are steeped in opaque, technical language. He does his best to help them put their roadmap in plain terms so a wider audience can understand the messaging. By broadening the description, analogs, or analogies both parties can work to develop “non industry” language that helps clear up pitch points, marketing, and positioning to use in day to day parlance.
Maybe it’s part of his Boston identity to encourage others to speak in plain language, but Dean has found it helps startups and audiences alike make messages travel further.
3 Career Insights / Learnings
Trust to Teach Yourself – “Don’t underestimate how much you can learn in 3-6 months. It’s easy to get intimidated by raw technical expertise or someone who’s been working on something for a long time. But you can get up to speed quickly by trusting your ability. Read a lot, do your research, and get to the point where you can speak the language and start learning from & understanding the experts.”
You Can’t Predict Your Path – “You can’t predict all the opportunities that will come your way. Most of us go through life constantly surprised by the decision points that arise. You can do your best to aim toward certain goals, but when an unexpected chance or challenge comes along, you have to be ready to dive in or address it head-on.”
Having A Macro View – “Constantly learn about big picture trends – geopolitical, local, and technological – and look at the whole market. Don’t just focus narrowly on what you’re doing. Keep your head on a swivel, look at everything around you, and always be contextualizing!”
Working at TiE has given Dean an immense respect for early stage entrepreneurs and he really enjoys getting to learn in a bunch of different areas, continuing to look for great people that he can build his career with. He loves the fact that he can’t predict what he’ll be doing in his 50’s.
You can find Dean putting in work all over Boston, recruiting startups for TiE’s accelerator program, or on LinkedIn. Thanks for sharing. Look forward to seeing all the teams, industries, and trends you impact in the coming years!