In Part 2 of this two-part deep dive, Triangle Tweener Talks host Scot Wingo sits down with legendary Triangle founder Mike Doernberg to explore his journey on scaling multiple companies, spinning out new ventures, navigating private equity, and why he never left North Carolina.

Tune in to hear:

• How ReverbNation grew from a side project into a 6M-artist platform
• The spin-out journey behind Adwerx, and why it worked
• Mike’s framework for identifying spinoff opportunities inside existing companies
• Why the team is the company, and why incubated teams can struggle
• The origins of PlayMetrics and the youth-sports system-of-record vision
• How Mike navigates private equity without losing culture or control
• What PE adds that venture capital often can’t
• What it’s like to scale from 25 people to 450+
• Mike’s long view on the Triangle startup ecosystem, then vs. now
• Why he never moved to the Bay Area
• Whether a Mike-led venture studio might be next 👀

Where to Find Mike Doernberg:

LinkedIn: https://www.linkedin.com/in/michaeldoernberg/
PlayMetrics: https://home.playmetrics.com/

Where to Find Scot Wingo:

• LinkedIn: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:
00:05 — Welcome to Part 2 with Mike Doernberg
00:12 — Coming back from “Home Depot retirement”
00:18 — The origin and explosive growth of ReverbNation
00:27 — Solving the cold-start problem before it had a name
00:33 — Building Promote.it → the foundation for Adwerx
00:42 — Spinning out Adwerx and structuring the deal
00:52 — Should Mike run a venture studio? Scott pushes him
01:00 — Why incubating ideas is easier than incubating founders
01:10 — The spinout challenge: talent dilution
01:15 — The path to PlayMetrics and modernizing youth sports
01:27 — Selling Reverb to focus fully on PlayMetrics
01:38 — Navigating private equity the right way
01:47 — How PE can empower (not suffocate) founders
01:55 — Running a 450-person org and learning a new leadership mode
02:03 — Why Mike stayed in the Triangle — and how the ecosystem evolved
02:16 — Triangle vs. Bay Area: culture, risk, and quality of life
02:30 — Final reflections & Scott’s challenge on a future venture studio
02:38 — Outro & sponsor thank-yous

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This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West.

We couldn’t share posts like this without our amazing sponsors:

Gold Sponsors:

• Balentine: https://www.balentine.com/triangle-entrepreneurs
• EisnerAmpner: https://www.eisneramper.com
• Robinson Bradshaw: https://www.robinsonbradshaw.com

Silver Sponsors:

• Automated Consulting Group: https://automated.co
• Bank of America: https://business.bofa.com/en-us/content/technology-industry-group.html

2025 Sponsors:

• Extensis HR: http://www.extensishr.com/

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

In Part 1 of this two-part deep dive, Triangle Tweener Talks host Scot Wingo sits down with legendary Triangle founder Mike Doernberg to explore the earliest chapters of his career, from CPA to multi-exit entrepreneur.

Mike walks through the founding of Marathon, the rise of early PC-driven consulting, the creation and spinout of SmartPath, raising capital through the old-school angel gauntlets, navigating the DoubleClick acquisition, and why “retirement” lasted all of three months.

Tune in to hear:

• What the early startup ecosystem looked like before the Triangle was “the Triangle.”
• The origins of Marathon and how the rise of PCs and early web consulting created new opportunities.
• How a project inside GlaxoSmithKline became the spark that turned into the SmartPath product.
• Mike’s philosophy for spinning out products successfully, and why strict separation is essential.
• Raising capital in the 90s and early 2000s: angel gauntlets, tough rooms, and memorable TIG stories.
• The SmartPath exit to DoubleClick and why Mike now believes they sold too early.
• How exiting young led him to a very short-lived “retirement” and why founders struggle to sit still.

Where to Find Mike Doernberg:

LinkedIn: https://www.linkedin.com/in/michaeldoernberg/
PlayMetrics: https://home.playmetrics.com/

Where to Find Scot Wingo:

• LinkedIn: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:
01:02 – Mike’s early background & move to NC
03:30 – Becoming a CPA but wanting more
05:54 – Early exposure to startups at Ernst & Young
07:50 – Why entrepreneurship became inevitable
09:50 – Story of Burl Software and Y2K
12:10 – How Marathon was formed
13:22 – Rising PC adoption and early web consulting
14:51 – Early e-commerce and building internet applications
17:00 – How the GlaxoSmithKline project inspired SmartPath
19:06 – The power of deeply understanding a customer problem
20:34 – Building early commerce & workflow applications
23:40 – SmartPath as an early low-code platform
24:59 – Why selling SmartPath was his biggest mistake
26:00 – Raising venture in the 90s & 2000s
28:20 – The TIG pitching gauntlet
30:00 – A founder’s early-career fear of the unknown
31:10 – The SmartPath exit to DoubleClick
33:00 – Life at DoubleClick & post-acquisition changes
35:20 – Mike retires for 3 months (Home Depot era)
36:50 – Why founders struggle not to build
38:45 – The addiction and community of company building

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This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

Mark Flickinger is the COO and General Partner at BIP Ventures, one of the Southeast’s most active venture firms. Based in Atlanta, Mark brings a rare dual perspective, an operator who scaled startups before joining the investing side. Since 2015, he’s helped BIP expand from an Atlanta-centric firm into a major player across the Southeast and Midwest.

Every year, BIP Ventures releases its State of Startups in the Southeast report, arguably the most comprehensive snapshot of our region’s innovation economy. In this episode, Scot sits down with Mark to break down the 2025 findings, from AI and valuations to where the capital is really flowing.

Tune in to hear:

• How the State of Startups in the Southeast report came to be, and why it’s become a key annual benchmark for founders and investors.
• The Southeast’s steady growth amid national volatility, and what that says about the region’s resilience.
• Why North Carolina now ranks #2 for capital invested, with a healthy mix of early, mid, and late-stage deals.
• The rise of AI-driven startups, not in infrastructure, but in real applied use cases driving revenue.
• Which investors and funds are most active across the region, from Triangle Tweener Fund to Hatteras, IdeaFund, and CoFounders Capital.
• How Atlanta continues to anchor Georgia’s innovation scene, with momentum in cybersecurity, fintech, and healthcare tech.
• Why balanced growth across industries is dampening volatility and attracting new waves of talent and capital.

Where to Find Mark Flickinger:

LinkedIn: https://www.linkedin.com/in/mark-flickinger-24295538/
BIP Capital: https://www.bipcapital.com/

Where to Find Scot Wingo:

• LinkedIn: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:
02:00 – Meet Mark Flickinger & the BIP Ventures origin story
05:30 – How the State of Startups report began
10:00 – What makes the Southeast data different
15:00 – Why the 2025 report matters
18:00 – Trends: AI, capital concentration, and valuation health
23:00 – The Southeast’s unique resilience
27:00 – North Carolina’s rise to #2 in regional investment
31:00 – Triangle Tweener Fund and other active players
37:00 – Atlanta’s current momentum and industry strengths
42:00 – What founders should take away from the data
46:00 – Closing thoughts and Mark’s advice for founders

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This episode of Triangle Tweener Talks is hosted by Scot Wingo, presented and produced by Triangle Tweener Fund, with creative assets and design support from Walk West.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

From the world of tech startups to the high-stakes world of sneakers, Walk West CEO and founder Greg Boone is a serial entrepreneur with a unique journey. With a background in computer science and a history of building and investing in companies, Greg brings a fresh perspective on how to navigate the current "AI tsunami."

Tune in to hear:

• Greg's entrepreneurial journey, from his computer science degree at North Carolina A&T to his early career at IBM and his ventures in everything from the bar industry to e-commerce.
• How his marketing agency, Walk West, is growing 30-40% year over year by helping clients adapt to a world where AI has disrupted traditional go-to-market strategies.
• His "Four P" framework for growth: Podcasts, Partnerships, Paid Media, and Public Relations, and why being "seen, heard, and cited" is critical for success in the age of AI.
• The concept of "personality-led growth" and why building trust and a personal brand is essential when abstract brands and ideas are losing their hold.
• Greg’s love for sneakers and what he collects.
• A fascinating conversation about Michael Jordan's business acumen, his brand effect, and his successful ownership of the Charlotte Hornets.
• The "Blockbuster moment" for Google and why they had no choice but to embrace AI.

Where to Find Greg Boone:

LinkedIn: https://www.linkedin.com/in/gregboone/

Walk West: https://walkwest.com/

Where to Find Scot Wingo:

LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo

In this episode:

(00:06:00) The evolution of Walk West from a marketing agency to a content studio.

(00:10:00) Greg’s "Four P" framework for business growth.

(00:16:00) Greg's entrepreneurial journey, including his background in computer science and his various ventures.

(00:23:00) A deep dive into sneaker collecting and the business of Michael Jordan.

(00:32:00) Walk West's growth and the importance of partnerships.

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

What happens after you sell a company you helped turn around?

For Dr. Doug Kaufman, it’s a story of new ventures and hard-won lessons.

In this second part of a two-part series, Doug discusses his time at TransLoc, a mass transit technology company he helped lead to a successful sale to Ford.

He shares how he navigated a challenging acquisition process and the importance of a strong, collaborative board. He also talks about the challenges of his most recent venture, Belongly, including the difficult decision to pivot the business and raise capital in a shifting market.

Now, as a Duke professor, executive coach, and partner at an AI consulting firm, Doug offers insights on the critical importance of founder mental health and the power of vulnerability in leadership.

Tune in to hear:

• Why Doug was initially hesitant to get involved with TransLoc, a company focused on "mass transit technology".
• The red flags he ignored when joining TransLoc , and how he turned the company around after discovering it was not financially healthy.
• How TransLoc expanded its services beyond tracking buses to create a "mobility network" and provide data-driven insights to transit agencies.
• The story of TransLoc's acquisition by Ford , and the delicate process of bringing a Fortune 15 M&A team back to the table after walking away.
• Dr. Kaufman’s philosophy on how to run a board, including the importance of setting clear roles and fostering a collaborative team environment.
• A candid account of his experience with his next startup, Belongly, and the painful lessons learned from market shifts and fundraising challenges.
• The psychological impact of founder ups and downs , and why Dr. Kaufman believes vulnerability is a "superpower" for entrepreneurs.

Where to Find Dr. Doug Kaufman:

LinkedIn: https://www.linkedin.com/in/drdougkaufman/

Where to Find Scot Wingo:

• LinkedIn: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:
(00:01:00) Dr. Kaufman describes how he got connected with TransLoc after leaving Spring Metrics. He initially thought "mass transit technology" was boring until a board member convinced him to talk to the founding CEO, Josh Whitten.
(00:06:00) Dr. Kaufman became the CEO and raised over $6 million in equity from investors like SJF Ventures and Fontinalis, and another $2 million in debt from Square One.
(00:11:00) Dr. Kaufman reveals that he and his team did walk away from the deal once.
(00:17:00) Dr. Kaufman describes the big idea behind Belongly as an effort to address the mental health crisis in young people
(00:28:00) Dr. Kaufman describes his specific type of executive coaching
(00:33:00) The conversation shifts to founder mental health.

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

What happens when a classically trained psychologist leaves the world of academia to shift careers?

For Dr. Doug Kaufman, it was to become a serial entrepreneur (obviously).

Doug's story is defined by a relentless curiosity about human behavior, a series of successful ventures, and some hard-won lessons in the chaotic world of startups.

In this first of a two-part series, Doug recounts his unconventional path from a psychology PhD to joining a hyper-growth tech company, starting his own bootstrapped business, and facing the ultimate test of a founder's resilience in the Triangle.

Tune in to hear:

• Why Doug left the academic track to start his own online education company and a side hustle to fund it.
• His experience in the early days of a hyper-growth startup at Blackboard, and why he eventually left to seek new challenges.
• The story of his move to the Triangle and the founding of his first company, ClearTXT, a one-to-many notification system for universities.
• The unexpected challenges he faced at ClearTXT, including a televised public relations crisis and a patent troll lawsuit.
• Why his bootstrapped company consistently beat a larger, VC-funded competitor in a head-to-head competition.
• The origin of Spring Metrics and his early lessons from joining the Triangle Startup Factory.
• A candid account of his first, disastrous board meeting, and the onset of "founder burnout" that led to a painful but necessary exit.

Where to Find Dr. Doug Kaufman:

LinkedIn: https://www.linkedin.com/in/drdougkaufman/

Where to Find Scot Wingo:

• LinkedIn: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:
(00:02:00) Dr. Kaufman's lifelong fascination with psychology, human behavior, and the personal reasons for his interest.
(00:04:00) The decision to leave academia to start his first company, Alley Dog, and a computer repair side hustle.
(00:08:00) Joining Blackboard in 1998 and his experience in a hyper-growth tech startup.
(00:15:00) Why he left Blackboard to move to the Triangle and start his own company.
(00:18:00) Founding ClearTXT and navigating a major PR crisis at a large university.
(00:24:00) The lessons he learned from the chaos of startup life, including a patent troll lawsuit and a successful acquisition.
(00:29:00) The origins of Spring Metrics and joining the Triangle Startup Factory's first cohort.
(00:37:00) A frank discussion about his first board meeting at Spring Metrics and the difficult experience that followed.
(00:44:00) His eventual transition out of the CEO role and the valuable lessons he took from the experience.

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

From her upbringing in Johannesburg, South Africa, to a career spanning Wall Street, an Ivy League MBA, and the early days of e-commerce, Ricci Wolman’s journey is a all about problem solving, resilience, freedom, and...the paradox of choice?

As the CEO and co-founder of Written Word Media, she has built a bootstrapped and profitable business by solving a problem her own mom faced: book discovery in a crowded market.

Tune in to hear:

• Ricci's immigration story from South Africa to the US and the culture shocks she faced along the way.
• Why she left a lucrative Wall Street job after 9/11 to pursue a more impactful career in microfinance.
• How her experiences at The Body Shop and Lulu Publishing laid the groundwork for her own entrepreneurial venture.
• The origin story of Written Word Media, which was inspired by her mom's self-published book and a realization about the "paradox of choice" on Amazon.
• Why the generous Amazon affiliate program in its early days acted as an unintentional seed fund for the business.
• The unique two-sided marketplace model that matches authors with hyper-personalized email newsletters for readers.
• Ricci's philosophy on "private barometers of success" and why bootstrapping allowed her to build a business aligned with her core values.
• Her passion project, The Flop.ai, a newsletter dedicated to demystifying AI and helping people overcome their fear of new technology.
• Her advice for young founders, including why it's okay to take risks and the value of a strong local community.

Where to Find Ricci Wolman:

LinkedIn: https://www.linkedin.com/in/ricciwolman/
Written Word Media: https://writtenwordmedia.com/
The Flop.ai: https://www.theflop.ai/

Where to Find Scot Wingo:

• LinkedIn: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:
(00:04:00) Ricci’s immigration from Johannesburg, South Africa and the major culture shock of moving to the US.
(00:11:00) Her path to Wall Street, working as an investment banking analyst at Bear Stearns, and leaving after 9/11 for a more impactful role.
(00:17:00) Running an e-commerce side hustle on a Yahoo store and the decision to get her MBA at Harvard Business School.
(00:24:00) The move to North Carolina and her career in e-commerce marketing at The Body Shop and Lulu Publishing.
(00:30:00) How her mom's self-publishing journey inspired the idea for Written Word Media.
(00:48:00) The birth of Free Booksy as a sandbox to test marketing and the accidental funding from the Amazon affiliate program.
(00:58:00) The decision to formally start the business with her husband, Ferol, who left ReverbNation to become her co-founder.
(01:04:00) The unique challenges of balancing the two sides of a marketplace business and keeping authors and readers happy.
(01:07:00) Ricci's bootstrapping philosophy and why she optimizes for "private barometers of success."
(01:14:00) Her new passion project, The Flop.ai, a newsletter to help demystify AI.
(01:18:00) Advice for founders on taking risks, choosing the right path, and leveraging the Triangle's supportive community.

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/

What happens when a North Carolina native, seasoned by Silicon Valley and Wall Street, returns home to build a company that marries profit with purpose? For Jason Massey, co-founder and CEO of Ndustrial, it's led to a 14-year journey developing cutting-edge technology that makes industrial facilities more efficient and sustainable.

In this episode, Jason shares his unique path, from a childhood in Mebane and studying physics and finance at NC State, to navigating the dot-com bubble in New York and the vibrant startup scene in Silicon Valley. He opens up about the "dysfunction" that birthed new companies from his own efforts and why he ultimately returned to his roots to build Ndustrial into a global leader in industrial energy management.

Tune in to hear:

• Jason's unexpected journey from Mebane, NC, to Wall Street, Silicon Valley, and back again, shaped by a series of "learning experiences."
• The wild story of his early angel investment in Tap Tap Revenge, a mobile game that became an App Store sensation.
• How the "dirty data plumbing" challenge in manufacturing led Ndustrial to pivot from a service business to a SaaS platform for industrial energy management.
• The critical insight that led to Ndustrial's first major product breakthrough: predicting and managing Coincident Peak energy charges for factories.
• Why Ndustrial embraces a hybrid model of SaaS and professional services, contrasting with traditional Silicon Valley expectations.
• His strategic approach to bringing in corporate venture capital from global giants like ABB and GS Energy.
• Jason's vision for Ndustrial, balancing profitability with environmental impact, and why they aim to build a "sustainable business" rather than chasing a quick exit.
• The company's significant work in the cold chain industry, including efforts to optimize food refrigeration and reduce energy consumption.
• The vital role of AI in industrial settings, particularly for contextualizing data and speeding up analysis, even amidst "dirty data."
• Jason's perspective on the Triangle's clean tech ecosystem and the responsibility entrepreneurs have to support each other by buying from local startups.

Where to Find Jason Massey:

LinkedIn: https://www.linkedin.com/in/jasonmnc/
Ndustrial: https://ndustrial.io/

Where to Find Scot Wingo:

• LinkedIn: https://www.linkedin.com/in/thescotwingo/
• Tweener Times: https://www.tweenertimes.com/
• X: https://x.com/scotwingo

In this episode:
(00:06:00) Growing up in Mebane, North Carolina, and his path to entrepreneurship through Wall Street and Silicon Valley.
(00:13:00) The velocity of failure in Silicon Valley and his first exposure to clean tech.
(00:17:00) Returning to North Carolina and settling in Mebane with his family.
(00:20:00) The Tap Tap Revenge angel investment and the lessons learned.
(00:28:00) The serendipitous founding of Sustainable Industrial Solutions (SIS) and building foundational tech with NC State engineering students.
(00:37:00) The pivot from SIS to Ndustrial, focusing on industrial production data and the Coincident Peak breakthrough.
(00:45:00) Why Ndustrial embraces a hybrid model of SaaS and professional services, and their approach to hardware.
(00:49:00) Ndustrial's $26 million fundraising journey and the strategic value of corporate VCs.
(00:53:00) Dominating the cold chain market and its massive energy and sustainability impact.
(01:02:00) The value of being "Switzerland" in the energy markets and building a truly sustainable business.
(01:10:00) The significant AI play at Ndustrial, using LLMs for contextualizing data and enhancing user interfaces.
(01:15:00) Jason's commitment to mentoring and supporting the Triangle's entrepreneurial community.

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Triangle Tweener Talks is hosted by Scot Wingo, presented by Triangle Tweener Fund, and produced by Walk West.

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Triangle Tweener Talks is sponsored by:

• Atomic Object: https://atomicobject.com/