The Latest Era of Swagger: Version 8

If you’ve been keeping up with Swagger's journey, version 8 will shock you. Changed rules, enhanced mechanics, and a redesigned board (wait what?), all of which collided in last month’s playtests in Toronto.

After running three sessions in May, we can finally see Swagger slowly evolve into what it is meant to be: playable, teachable, and fun.

Putting the board in board game.

Let’s begin with one of the biggest changes: the board.

In earlier versions, the game leaned heavily on verbal facilitation and shared table space. Now, Swagger v8 has a visual board that mirrors real-life startup journeys. The layout clearly maps each company’s path through Series A, B, and C, with assigned slots for fundraising and IPOs. It is also easier to track who’s in which round, and understand how your portfolio is performing.

The redesign gives each player their own portfolio board, creating a personal dashboard for tracking company growth and co-investments.

New mechanics.

Gameplay in v8 follows the same streamlined structure: Company Selection → Growth → Fundraising. That cycle gives Swagger a reliable framework, eases the learning curve for new players, and allows for the game to be played again and again.

Changes:

• Fundraising Environment cards now set different conditions for each year. Players don’t control the market, they respond to it. This emphasizes the power of luck in VC, a factor that players (and some VCs) often struggle to get comfortable with.
• We introduced the concept of Advice cards which allow players to give good (or bad) advice to their companies. We wanted to introduce more player interaction. You choose your answer in secret, then the other players vote. If your answer matches the majority, you gave good advice and increased the growth of the company.

• Swagger is its own currency now: it can get you through crises, boost fundraising efforts (part of the Fundraising Environment cards), and unlock strategic plays in co-investments.

Playtesting feedback.

In Toronto, we tested Swagger v8 with three different groups at Highline Beta and Schulich Startups. Swagger isn’t perfect—a key reason why we playtest in the first place. What actually matters is the feedback that helps us get a step closer to the best version possible.

They liked the strategic flow, but still struggled to climb the steep learning curve. There was also confusion about roles: are players acting as VCs, founders, or both?

The Advice card sparked heated rounds, discussions, and betrayal which was fun, but also subject to manipulation when players prioritized sabotage over realism. This led to the questions about who the players represented. If they are the founders, is it realistic for them to set the VC up for failure by supporting bad advice, rather than good advice? 

Yes, the physical board was a major hit. However, from a user experience standpoint, reading upside down and having to take pictures of the company cards wasn’t an ideal strategy and we plan on fixing this in the next version.

The biggest recurring request? Bring back the Monopoly money. The poker chips didn’t make the cut and players missed the feeling of holding cash in their hands more than anything. Sometimes, the act of paying with cash can be more emotionally fulfilling than paying with anything else.

The bottom line.

While the playtest sessions proved the game is fun, it also showed what’s missing.

Two key issues remain: the game still lacks an efficient setup process, and the roles for providing advice are unclear. The board needs a better design and the idea of career progression, which was removed in V8, was misssed.

Version 8 is not the finish line for Swagger. That means… more updates and playtests are just around the corner. Subscribe to be the first to experience what’s next.