Alright – so today we’ve got the honor of introducing you to Caroline Dennis. We think you’ll enjoy our conversation, we’ve shared it below.
Alright, Caroline thanks for taking the time to share your stories and insights with us today. How did you come up with the idea for your business?
The name of my business, Two-Degrees.io, and my title, Disruptive Industry Agent, both hold special significance to me. Two-Degrees is a play on the term “six degrees of separation,” a concept I have long found fascinating. My initial foray into the technology industry began with my husband when we co-founded two companies. Our first venture, Wired Nation, was an IT and Security consulting firm that we ran together for 17 years. The second, Grappa Wireless, was a wireless Internet Services Provider that we operated with another co-founder for 5 years. Both companies were based in Santa Fe, New Mexico.
Those years were profoundly impactful for me both personally and professionally. We worked with a variety of industries and built a strong reputation in the region, driven by our passion for building trust with our clients and the larger community in the Southwest. I became heavily involved in economic development and professional technology communities in New Mexico, particularly in IT, Cybersecurity, Robotics, and STEM education.
One thing that always struck me was the siloed nature of many technology professionals. For example, those in information security often had little knowledge of what was happening in robotics or STEM education, despite the intersections between these fields. This realization became more apparent when I joined technology boards, community college advisory boards, and other nonprofits focused on STEM education. I discovered that I had a knack for understanding a wide range of technologies and how they could be integrated to foster collaboration within communities. I enjoy thinking of it as fitting pieces of a puzzle together, where adjacent technologies can complement each other.
The title “Disruptive Industry Agent” evolved from my extensive experience as a mentor and career coach. After selling both companies and moving to Maine, I adopted the title “Career CoolHunter” due to my work as a career advisor and coach to students and professionals across various industries. In my current role, I help founders, organizations, and communities grow market share, build products, or start initiatives. It encompasses a wide range of activities, but at its core, it involves bringing together innovative people to create impactful solutions through science and technology.
Caroline , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
About Me
As a two-time IT Security and Internet Services Provider startup founder, I’ve worked across various industry verticals, helping companies, nonprofits, and organizations navigate and keep pace with evolving business challenges. My industry expertise spans Blockchain, DAOs (Decentralized Autonomous Organization), NFTs, VR/AR/MR, Robotics, IT Security, Precision Medicine, AI & NLP (Natural Language Processing). I’m passionate about bringing together people from diverse technical, creative, and scientific communities to co-create a future that promotes human flourishing and planetary health.
My Role and Company
I’m a Disruptive Industry Agent and founder of Two-Degrees.io, a consulting practice that helps startup founders and organizations grow and scale market share across adjacent industries. My work focuses on curating actionable ways to engage industry communities, companies, and leaders to align market fit and grow product customer bases. This practice is built on nearly three decades of experience in entrepreneurship, technology, healthcare, and higher education.
What Sets Me Apart
Depth of industry knowledge across emerging technologies
Creative approach to facilitating actionable connections
Commitment to inclusivity and humanity
Current Projects
An immersive Co-host & advisory board member for VRAR Chicago the Next Evolution, a monthly hybrid meetup about immersive technology
Leadership team member of XR Women, a pioneering global community of women and allies building an inclusive spatial computing future
Part of Symphony, a global accelerator for Sustainable Smart Cities
Member of the IEEE working group building the framework for Sustainable Smart Cities dedicated to human and planet health for the future
Working with an incarcerated graduate student championing a Maine initiative building VR and AR career development training for incarcerated persons
Leading an effort to improve mental health support and scalability solutions for teens in Maine
My Background
My expertise as an industry catalyst in web3, Blockchain, XR, Precision Medicine, and Cybersecurity stems from:
Over a decade in Institutional Advancement at prestigious institutions
Successfully building and selling IT Security Services and wireless Internet companies
Developing digital accelerated learning and mentoring programs at universities
Advising Blockchain education startups
Serving on numerous technology and economic development boards
This diverse background allows me to bring a unique perspective to solving complex problems and fostering innovation across industries.
Conversations about M&A are often focused on multibillion dollar transactions – but M&A can be an important part of a small or medium business owner’s journey. We’d love to hear about your experience with selling businesses.
Selling Our Businesses
My husband and I co-founded and ran two companies together for nearly 18 years, with a 5-year overlap where we managed both simultaneously. Selling these businesses was an emotional experience. Our first company, Wired Nation, felt like our firstborn. We poured our hearts and souls into it, and we’re incredibly proud of what we accomplished.
Key Achievements
Maintained long-term customer relationships, some lasting all 17 years
Successfully transitioned every customer to the new owners upon sale
Received numerous awards for service and innovation
Built strong, personal connections with customers and employees who watched our family grow
Lessons Learned
Valuing Your Business: The selling process taught me a lot about how to properly value a business and what makes a business model attractive to potential buyers.
Adaptability: Our first attempt to sell Wired Nation led us to pivot and build a managed services business model, which ultimately increased our recurring revenue and made us more attractive to buyers.
Finding the Right Fit: We sold Wired Nation to a local company looking to expand their wiring infrastructure business, which proved to be a good match.
Industry Knowledge: Selling our internet company, Grappa Wireless, required understanding industry trends, such as the consolidation of WISPs (Wireless Internet Service Providers) in our region.
Relationship Building: Both sales processes emphasized the importance of building trust and relationships. Our Grappa Wireless buyer even became a friend and colleague.
Timing and Personal Goals: After selling both companies, we decided it was time for a change and moved to Maine to be closer to family.
Advice for Entrepreneurs
Balance is Key: Juggle work life, personal life, and various aspects of your business (operations, employees, vendors, marketing, customer service, sales).
Maintain a 360-Degree View: Especially important in professional services and technology businesses.
Build Trust: Focus on doing good work and building strong relationships with customers, employees, and vendors.
Be Open to Pivoting: Sometimes, the process of preparing to sell can lead to valuable improvements in your business model.
Understand Your Industry: Know the trends and what makes your business attractive to potential buyers in your specific sector.
Prepare Emotionally: Selling a business you’ve built from the ground up can be an emotional process. Be prepared for the personal impact.
What do you think helped you build your reputation within your market?
Building my reputation across a broad market has been a multifaceted process:
Diverse Expertise: My knowledge spans various technologies and sectors, which piques people’s curiosity.
Engaging Communication: I use all forms of collaboration platforms – in person, virtual, and an everchanging host of metaverse platforms to connect and learn.
Listening and learning from mentors, colleagues of all ages and backgrounds.
Active Networking: I engage in conversations across platforms like LinkedIn, Discord, and Slack, constantly learning and exchanging ideas.
Continuous Learning: I regularly attend webinars, elearning, conferences, and volunteer, keeping my knowledge current across tech, science, planetary, and human health domains.
Giving Back: I often offer resources, mentoring and connections beyond my consulting work, fostering a non-transactional approach to relationship-building.
Regular Engagement: On average, I meet new founders or professionals weekly, expanding my network and knowledge base.
Transparency: I’m open about what I don’t know, a lesson learned from IT consulting where clear communication is crucial.
Adaptability: I demonstrate how my skills in curating connections and creating strategies can be applied across various products or projects.
Visibility: I maintain an active online presence, making it easy for potential clients to find and understand my work.
Value-Added Approach: I focus on providing actionable strategies for activating people and growing or scaling products and projects.
This combination of broad expertise, active engagement, continuous learning, and transparent communication has helped build trust and credibility across diverse sectors.
Contact Info:
- Website: https://www.two-degrees.io/
- Linkedin: https://www.linkedin.com/in/carolinedennis1/
- Twitter: @CarolineADennis
- Other: This recording tells more about me: https://the-project-login-podcast.simplecast.com/episodes/caroline-dennis-ixuOm_Db
Image Credits
XRWomen, NoWhere.io, AltSpace (RIP)