Guess Where Trips

Jessica Off
London, ON

Jessica Off pitching Guess Where Trips on Dragons’ Den

The pitch

Jessica Off from London, ON, pitched Guess Where Trips in Season 19, Episode 6, asking the Dragons for $250K for 5% of the company.

  • Asked for$250K for 5%
  • Valuation$5Mimplied by the ask
  • OutcomeDealwith Arlene Dickinson and Brian Scudamore
  • Final deal$250Kplus a royalty: 5% royalty until 3x money back, then 2% in perpetuity

Offers in the Den

DragonOfferResult
Manjit MinhasNo offer, felt founder didn't need a Dragon and could grow on her ownOut
Michele Romanow$250,000 for 10% equity plus 5% royalty until double her money backDeclined
Arlene Dickinson$250,000 for a 10% royalty until 4x money backWithdrawn
Brian ScudamoreJoint offer with Arlene DickinsonAccepted
Wes Hall$250,000 for 5% royalty until 3x money back, then 2% in perpetuity, no equity given upDeclined

Jessica Off, from London, Ontario, asked for $250,000 for 5% equity in Guess Where Trips, a one-day surprise road trip company. Customers receive sealed envelopes revealing stops along a themed route, with a paper guide costing $65 or a digital PDF for $39; the company offers over 100 itineraries and has served about 110,000 customers. The business has done about $6 million in sales to date, with $2.5 million last year and a projection of $5 million this year after launching in the US, with EBITDA margins around 55% and net margins around 45%; marketing spend was about $180,000 last year, and 92% of sales are currently in Ontario.

Manjit Minhas went out, feeling the founder did not need outside help. Michele Romanow offered $250,000 for 10% equity plus a 5% royalty until double her money back, which was declined. Arlene Dickinson and Brian Scudamore made a joint offer of $250,000 for a 10% royalty until 4x money back, which Jessica Off accepted, while Wes Hall's competing royalty-only offer was declined.

Pitch details from CBC’s Dragons’ Den pitch page.

Guess Where Trips today

  • StatusIn businessLast checked September 2026

Guess Where Trips is still operating and sells through its website.