Dennis Volpe

Leadership Coach | Small Business Coach | Director, Leadership Research Institute | Navy Veteran & Mentor | Forbes Coaches Council Contributor | Author: “Transition On Purpose” | Small Business & Entrepreneurial Investor

📍 Greater Boston, United States🔄 Updated September 2026💼 8 investments📅 6 years investing🗓 Last invested Mar 2025
VC🌍 United States
8
Total investments
1
Early stage
3
Mid stage
3
Late stage
6y
Years active

Portfolio

8 investments · sorted by recency
All investments
Early stage
Mid stage
Late stage
Investor and Advisor
Mar 2025
Shift Group bridges the gap between military veterans, former athletes, and the business world through coaching and career upskilling. Our mission is to help these individuals unlock their unique skills and experiences and match them with top-tier companies in need of resilient, coachable, and team-oriented professionals. The Shift Connect platform accelerates learning and streamlines the hiring process by connecting employers with pre-vetted candidates who are ready to excel. Customers reduce hiring time, lower costs, increase growth rates, and improve retention. Shift Group is committed to helping businesses build high-performing teams and supporting veterans and athletes in their career development.
Investor and Advisor
Mar 2025
In 2017, Army Ranger and Aviator Dean Wegner created Authentically American® to help bring jobs back to America by selling competitively priced, premium branded apparel. Our initial focus is on providing Corporate and Organization Branded Apparel and Accessories. Our expertise, high-quality products, and superior customer service position us as the preferred Made in USA partner for all-size companies, nonprofits, teams, schools, and events! All of our shirts, jackets, socks, hats, and accessories are Made in America, so you, your business, school, or non-profit organization can be confident youre supporting American workers when you buy from us.
Investor and Contributor
Mar 2025
Leaderly is the first continuous leader development application in the world, marrying science and psychology to grow leaders at all levels of an organization. Leaderly is made for teams and designed to unleash the natural state of leadership in every person. Now available on iOS under invitation. CulturePop is the fastest growing culture growing & microlearning app in the world that doesn’t need a profile. It is designed for growing the data-driven and inclusive culture. CulturePop AI is continually learning and adjusting based on factors that we have geared in the system which do not require personally identifiable information. What determines employee experiences with different surveys, knowledge questions, analytics and content does not rely on PII but by other learning and engagement factors. CulturePop remembers where you are in learning and engagement, without having to know or track who you are. This unique design accelerates culture competency and authenticity in employee engagement. By freeing someone up from the social pressure concerns or privacy fears, the CulturePop system purely functions to help a person increase their awareness of their organization culture, it’s values and naturally improves their inclusion instincts. Leaderly and CulturePop are made by experts in behavioral sciences, leadership, AI and data science.
Investor
Jun 2024
Tozuda (Techstars Boston 21) is a company that makes impact indicators for head injury awareness and helmet damage indication. Our patented, non-electronic technology makes it easy to know when to check your head. Our mission is to make head safety accessible for helmet wearers with our innovative and simple solutions. Tozuda Head Impact Indicators can be attached to or integrated with all helmet types. If its RED, check your head.™
late stageManufacturing
Seed Investor
Mar 2024
Nooks is tackling the challenging necessity of Classified-Infrastructure-as-a-Service (CIaaS) for both industry and government customers to accelerate collaboration, technology adoption and engagement between industry and government to win the Great Power competition. Nooks will lower the barrier-of-entry/scale to qualified companies to engage in classified environments to rapidly bring innovative solutions to reality and revolutionize the landscape of classified operations. We strive to build a culture of "People First, Service Always." We are a Veteran Owned Small Business, and we believe that service to country can continue even after leaving the military/government. We want each of our employees to grow, learn, and achieve more than they ever thought possible in a culture that embraces diverse backgrounds and perspectives. Come join our team!
Investor
Nov 2020
Leaders in the craft cold brew coffee space. We are purveyors of specialty coffee sourced from all over the world, focusing on connecting people through their coffee.
Investor - Strategic Advisor
Nov 2020
If youre a growth-minded veteran inside the immediate transition window or have been out for years, have realized that immediate transitional education has a shelf life to your goals and aspirations after basic needs are met, and are looking for the #goldengrenades to get yourself out of your own way and fuel your desire to make an impact post-military. This is your podcast built by veterans for veterans as we dive into the trenches with today’s top subject matter experts, share inspiring transition stories, and provide masterclasses to equip you to reach your full potential.
Board Member
Apr 2020
Patriot Resilient Leader Institute (PRLI), a 501 (c)(3) organization, recognizes that those who have served their country and communities often need a helping hand in order to recover and maintain their mental and physical health. By running Camp Resilience retreats for military service members, veterans, first responders, and their loved ones, PRLI does its part to help those who have served bounce back in mind, body, and spirit. Located in the beautiful Lakes Region of New Hampshire, Camp Resilience retreats combine outdoor experiential learning activities, facilitated peer-to-peer counseling, and life skills workshops and are often facilitated by active/retired VA clinicians. PRLI is devoted to tackling an array of issues affecting veterans and first responders—we offer a wide variety of tailored retreats that take the healing process out of the clinic and stress the importance of camaraderie and wellness in fostering resilience and recovery. We have found great success in running retreats for families, couples, and veterans coping with military sexual trauma, post traumatic stress, or moral injury. Founded in 2014 by a small group of veterans and local citizens, PRLI has welcomed over 1300 participants to 115 Camp Resilience retreats. The grass roots nature of our programs sends an important message to our attendees—their service is appreciated by their fellow citizens. PRLI is a primarily volunteer organization with five staff member and a dedicated Board of Directors comprised of Veterans, First Responders and mental health professionals. The Mission Using the scenic beauty of the Lakes Region of New Hampshire, the Patriot Resilient Leader Institute runs Camp Resilience for service members, veterans, first responders, and their loved ones. Camp Resilience retreats combine facilitated peer-to-peer counseling and outdoor experiential learning activities to help attendees to improve their physical, mental, and emotional well-being.
Experience · 15 entries
All (15)
Investments (8)
Founder (1)
Board (1)
2025
Investor and Advisor
Mar 2025
Shift Group bridges the gap between military veterans, former athletes, and the business world through coaching and career upskilling. Our mission is to help these individuals unlock their unique skills and experiences and match them with top-tier companies in need of resilient, coachable, and team-oriented professionals. The Shift Connect platform accelerates learning and streamlines the hiring process by connecting employers with pre-vetted candidates who are ready to excel. Customers reduce hiring time, lower costs, increase growth rates, and improve retention. Shift Group is committed to helping businesses build high-performing teams and supporting veterans and athletes in their career development.
Investor and Advisor
Mar 2025
In 2017, Army Ranger and Aviator Dean Wegner created Authentically American® to help bring jobs back to America by selling competitively priced, premium branded apparel. Our initial focus is on providing Corporate and Organization Branded Apparel and Accessories. Our expertise, high-quality products, and superior customer service position us as the preferred Made in USA partner for all-size companies, nonprofits, teams, schools, and events! All of our shirts, jackets, socks, hats, and accessories are Made in America, so you, your business, school, or non-profit organization can be confident youre supporting American workers when you buy from us.
Investor and Contributor
Mar 2025
Leaderly is the first continuous leader development application in the world, marrying science and psychology to grow leaders at all levels of an organization. Leaderly is made for teams and designed to unleash the natural state of leadership in every person. Now available on iOS under invitation. CulturePop is the fastest growing culture growing & microlearning app in the world that doesn’t need a profile. It is designed for growing the data-driven and inclusive culture. CulturePop AI is continually learning and adjusting based on factors that we have geared in the system which do not require personally identifiable information. What determines employee experiences with different surveys, knowledge questions, analytics and content does not rely on PII but by other learning and engagement factors. CulturePop remembers where you are in learning and engagement, without having to know or track who you are. This unique design accelerates culture competency and authenticity in employee engagement. By freeing someone up from the social pressure concerns or privacy fears, the CulturePop system purely functions to help a person increase their awareness of their organization culture, it’s values and naturally improves their inclusion instincts. Leaderly and CulturePop are made by experts in behavioral sciences, leadership, AI and data science.
2024
Investor
Jun 2024
Tozuda (Techstars Boston 21) is a company that makes impact indicators for head injury awareness and helmet damage indication. Our patented, non-electronic technology makes it easy to know when to check your head. Our mission is to make head safety accessible for helmet wearers with our innovative and simple solutions. Tozuda Head Impact Indicators can be attached to or integrated with all helmet types. If its RED, check your head.™
late stageManufacturing
Seed Investor
Mar 2024
Nooks is tackling the challenging necessity of Classified-Infrastructure-as-a-Service (CIaaS) for both industry and government customers to accelerate collaboration, technology adoption and engagement between industry and government to win the Great Power competition. Nooks will lower the barrier-of-entry/scale to qualified companies to engage in classified environments to rapidly bring innovative solutions to reality and revolutionize the landscape of classified operations. We strive to build a culture of "People First, Service Always." We are a Veteran Owned Small Business, and we believe that service to country can continue even after leaving the military/government. We want each of our employees to grow, learn, and achieve more than they ever thought possible in a culture that embraces diverse backgrounds and perspectives. Come join our team!
Show all 15 entries ↓
Investment activity
2020–2025 · 8 investments
202032024220253
Recent (last 2 years)Earlier