Three Companies, One Brand: Building Offline Over 13 Years with David Shaner
Thu Feb 05 2026
This is Part 1 of a two-part conversation. In this episode, we focus on Offline’s origin story and business evolution, not AI (yet).
Highlights from Part 1
Offline has effectively been three different companies under one brandEarly versions tried to reinvent Meetup, and failedA city-guide app reached ~3M people/month but couldn’t monetizeConsumer businesses can look successful while quietly breakingSubscription was the first model that truly workedRestaurants don’t want “deal seekers”, they want incremental revenueOffline works because it optimizes excess capacity, not discountsCOVID forced a near-shutdown, and a total rethink of operationsToday, Offline runs across 10 cities with ~600 restaurants and ~10,000 subscribersMost founders only hear about the winning version of a company. This episode shows the cost of getting there: years of pivots, wrong turns, false confidence, and learning, sometimes the hard way, how markets actually work.
Offline didn’t succeed because of a clever growth hack. It survived because David kept learning, iterating, and refusing to confuse traction with sustainability.
Where to Find David Shaner:
LinkedIn: https://www.linkedin.com/in/davidshaner/
Offline Media: https://www.letsgetoffline.com/
Where to Find Scot Wingo:
LinkedIn: https://www.linkedin.com/in/thescotwingo/
Tweener Times: https://www.tweenertimes.com/
X: https://x.com/scotwingo
Timestamps00:00–02:30 – Introduction & what this two-part series will cover02:30–05:30 – David’s background, NC State, and discovering entrepreneurship05:30–08:00 – The original idea: human connection in a screen-first world08:00–11:30 – Era 1: trying (and failing) to reinvent Meetup11:30–13:30 – Era 2: city guides, millions of users, zero monetization13:30–15:40 – Era 3: subscriptions finally click15:40–17:30 – COVID, near shutdown, and survival17:30–23:30 – Why restaurants accept discounts (the airplane seat analogy)23:30–25:30 – Why Groupon failed restaurants — and why Offline didn’t25:30–44:00 – Productivity, systems thinking, and process obsession44:00–45:10 – What’s coming in Part 2---
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/
------Triangle Tweener Talks is sponsored by:
Atomic Object: https://atomicobject.com/
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This is Part 1 of a two-part conversation. In this episode, we focus on Offline’s origin story and business evolution, not AI (yet). Highlights from Part 1 Offline has effectively been three different companies under one brandEarly versions tried to reinvent Meetup, and failedA city-guide app reached ~3M people/month but couldn’t monetizeConsumer businesses can look successful while quietly breakingSubscription was the first model that truly workedRestaurants don’t want “deal seekers”, they want incremental revenueOffline works because it optimizes excess capacity, not discountsCOVID forced a near-shutdown, and a total rethink of operationsToday, Offline runs across 10 cities with ~600 restaurants and ~10,000 subscribersMost founders only hear about the winning version of a company. This episode shows the cost of getting there: years of pivots, wrong turns, false confidence, and learning, sometimes the hard way, how markets actually work. Offline didn’t succeed because of a clever growth hack. It survived because David kept learning, iterating, and refusing to confuse traction with sustainability. Where to Find David Shaner: LinkedIn: https://www.linkedin.com/in/davidshaner/ Offline Media: https://www.letsgetoffline.com/ Where to Find Scot Wingo: LinkedIn: https://www.linkedin.com/in/thescotwingo/ Tweener Times: https://www.tweenertimes.com/ X: https://x.com/scotwingo Timestamps00:00–02:30 – Introduction & what this two-part series will cover02:30–05:30 – David’s background, NC State, and discovering entrepreneurship05:30–08:00 – The original idea: human connection in a screen-first world08:00–11:30 – Era 1: trying (and failing) to reinvent Meetup11:30–13:30 – Era 2: city guides, millions of users, zero monetization13:30–15:40 – Era 3: subscriptions finally click15:40–17:30 – COVID, near shutdown, and survival17:30–23:30 – Why restaurants accept discounts (the airplane seat analogy)23:30–25:30 – Why Groupon failed restaurants — and why Offline didn’t25:30–44:00 – Productivity, systems thinking, and process obsession44:00–45:10 – What’s coming in Part 2--- 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/ ------Triangle Tweener Talks is sponsored by: Atomic Object: https://atomicobject.com/