Founders as Sysops: The Forgotten Heroes of BBS Culture

Before Slack channels, Discord servers, or even web forums, there were bulletin board systems (BBS). Dial-up lines, screeching modems, and ANSI art were the backdrop, but the real characters of that era were the sysops (system operators). They were part technologist, part janitor, part community manager, and in many ways, the earliest archetype of what we now call Startup founders.

The Sysop as Startup Founders

Running a BBS was not a passive hobby. It required vision, persistence, and an unusual combination of technical and social skills. A sysop would:

If this list feels familiar, it’s because it is nearly identical to what early-stage founders do. In the same way that today’s solo founders spin up landing pages, handle customer support, write blog posts, and pitch investors, sysops wore every hat possible. They were the original “full-stack operators.”

T-Shaped Skills Before the Term Existed

In management literature, we talk about T-shaped skills:1 breadth across many disciplines with depth in one. Sysops embodied this decades before it was a buzzword.

The T-shape wasn’t optional. Without breadth, the board would collapse under technical or social strain. Without depth, it was just another generic dial-up number with nothing unique to offer. The same is true for founders: survive by knowing enough of everything, thrive by knowing one thing deeply.

Rabbit Holes and Big Pictures

Founders often talk about “rabbit holes”:7 disappearing into the fine detail of code, a new market, or some obscure regulatory quirk. Sysops knew this well. A single modem configuration line could consume hours of troubleshooting. Customizing ANSI menus required an obsession with color codes and ASCII values.

But sysops also needed to zoom out. They had to consider why people referred to their board. Was it the message base, the file library, or the sense of belonging? They had to watch trends, were callers moving to faster 2400 baud boards, or were networks like FidoNet creating demand for new features?

This dance between rabbit hole and big picture is precisely what founders live with today. Getting too caught up in the details can lead to burnout. Too much in the clouds, and you build castles that nobody uses. The sysop’s skill was balancing both.

Communities as Products

A BBS wasn’t just software and phone lines; it was a place. The sysop wasn’t only managing bytes; they were curating culture. Rules were posted like primitive Terms of Service, and reputation was earned through contribution, not likes or followers. Regular callers became moderators, and flame wars8 became lessons in governance.

Modern founders face the same truth: product and community are inseparable. The stickiest apps are the ones that feel like places you belong, not just tools you use. Sysops understood this instinctively.

Forgotten Heroes

Why forgotten? Unlike today’s startup founders, sysops rarely became rich or famous. Their reward was local notoriety, maybe a shout-out in a text file passed around, or the thrill of seeing twenty people dial in over a weekend. They weren’t scaling to millions, but they were the pioneers. They showed what it meant to bootstrap, experiment, and hold together a fragile system through sheer willpower.

Every Discord server, every Reddit community, every indie SaaS founder today stands on the shoulders of these unsung sysops.

Well…

  1. Wear every hat with intent. The grind is not glamorous, but it teaches resilience.
  2. Be T-shaped. You don’t need mastery in all things, but ignorance is fatal.
  3. Balance rabbit holes with vision. Dive deep, but surface often to chart direction.
  4. Community is the product. Technology without culture is an empty shell.
  5. Legacy matters. Even if you don’t IPO, the culture you build can echo for decades.

  1. T-shaped skills describe a person who has broad knowledge across multiple areas (the horizontal bar of the T) while also possessing deep expertise in one domain (the vertical bar). This mix allows them to collaborate across disciplines while still contributing specialized value. In startups and product teams, it balances adaptability with mastery. ↩

  2. ANSI art boards were BBS systems that showcased artwork created using extended ASCII characters and ANSI color codes. These boards turned text-based terminals into vibrant galleries with logos, animations, and stylized menus. Artists competed in “art packs,” pushing the limits of what could be drawn with characters and 16 colors. They became a cultural hallmark of the BBS era, blending technology and underground digital creativity. ↩

  3. Warez trading was the underground exchange of pirated software, games, and digital content on BBS systems during the 1980s and 1990s. Sysops often hosted secret file sections where users could upload and download cracked programs. This scene spawned release groups that added “cracktros” or signature screens to mark their work. While illegal, warez culture pushed technical boundaries and fostered tight-knit communities of hackers and traders. ↩

  4. FidoNet was a worldwide amateur computer network that connected bulletin board systems (BBS) in the 1980s and 1990s. It allowed users on different local boards to exchange private messages and public forum posts through scheduled dial-up calls between systems. Messages were bundled into “packets,” compressed, and sent overnight to save on long-distance costs. The network was decentralized, run entirely by volunteers, and organized by zones and nodes. FidoNet became one of the earliest large-scale, grassroots digital communities, foreshadowing today’s global internet forums and messaging systems. ↩

  5. Ham radio, or amateur radio, is a hobby and service where licensed operators use designated radio frequencies to communicate across local, regional, and global distances. Enthusiasts build or modify their own equipment, experiment with antennas, and connect during emergencies when other systems fail. Many early BBS sysops were also ham operators, blending radio and computing cultures. The shared spirit was exploration, community, and pushing the limits of communication technology. ↩

  6. Dungeons & Dragons (D&D) is a tabletop role-playing game first published in 1974 that lets players create characters and embark on collaborative adventures guided by a Dungeon Master. It combines storytelling, dice-based rules, and imagination to build immersive fantasy worlds. In the BBS era, D&D communities flourished as players shared campaigns, rules, and text-based roleplay online. The game’s culture of creativity and collaboration strongly influenced digital forums and early online communities. ↩

  7. Rabbit holes describe the experience of diving deeply into a specific topic, often losing track of time as one detail leads to another. In tech and startups, it reflects the tendency to obsess over configuration quirks, niche research, or fine-grained optimizations. While rabbit holes can uncover valuable insights, they also risk distraction if not balanced with a broader view of goals and strategy. ↩

  8. Flame wars were heated, often hostile exchanges between users on early online forums and BBS message boards. They usually began with disagreements that escalated into long threads of insults and personal attacks. While disruptive, flame wars also forced communities and sysops to develop moderation rules and governance practices. They highlighted the challenges of digital discourse long before social media amplified them. ↩