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Top 20 Travel Angel Investors in Canada in May 2025

Last updated: May 2025 A list of 20 angel investors that invest in Travel startups based in Canada. We rank investors based on the number of investments they made in Travel companies from Canada. We update this investor list every month.

Top 20 Travel Angel Investors in Canada in May 2025

Investor	Travel Canada investments
Peter M. Kern	4
Jesse Kaplan	2
Rasool Rayani	2
Lasse Järvinen	2
Mikko Nurminen	2
Stephen Curry	2
Stuart MacDonald	2
Andrew Kitchell	1
Jeffery H. Boyd	1
Andrew Wilkinson	1
Micheal Hyatt	1
Neil Wainwright	1
Steven Myhill-Jones	1
LP Maurice	1
Jamie McDonald	1
Jimmy G.	1
Lauri Sommarberg	1
David Arnsdorf	1
Rajiv Khaneja	1
Mike Liverton	1

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Peter M. Kern has been a director of Expedia since completion of the IAC/Expedia Spin-Off.Peter Kern is a Managing Partner of InterMedia Partners, LP, a private equity firm.Prior to joining InterMedia, Mr. Kern was Senior Managing Director and Principal of Alpine Capital LLC.Prior to Alpine Capital, Mr. Kern founded Gemini Associates in1996 and served as President from its inception through its merger with Alpine Capital in 2001.Prior to founding Gemini Associates,Peter Kern was at the Home Shopping Network and Whittle Communications.Since April 2013,Peter Kern has served as Chairman of the Board of Directors of Hemisphere Media Group, Inc., a publicly-traded Spanish-language media company.Mr. Kern also serves on the boards of a number of private companies, including Televicentro of Puerto Rico, LLC, Luxury Retreats International Holdings, Inc. and Cine Latino, Inc.Mr. Kern holds a B.S. degree from the Wharton School at the University of Pennsylvania.

Investment focus

Travel, Mobile, E-Commerce
Series A, Seed, Series B
Canada, United States

Portfolio highlights

Busbud — Travel the world by bus. Compare and easily book bus tickets from thousands of bus companies for your next destination with Busbud.
Snapcommerce — A new way to shop that maximizes savings, benefits and rewards on mobile.
Super.com — Through rich rewards and everyday savings, Super helps you access more of what you want at better prices, escape overspending, and level up life.

Jesse Kaplan

Investment focus

SaaS, Mobile, Travel
Seed, Series A, Funding Round
Canada

Portfolio highlights

Buyosphere —
GuestDriven — GuestDriven is a hospitality-focused guest engagement solution. We help hotels directly interact with guests, learn their preferences, build relationships and upsell inventory through personalized, moment-based targeted offers and communications.Guests are empowered with the ability to personalize and take full control of their stay, resultingin higher satisfaction, better reviews and more brand advocates.Founded in 2010 and headquartered in Montreal, Canada, GuestDriven has implementations in over 60 cities worldwide. Our team is dedicated to revolutionizing the most universal industry in the world.

Rasool is a serial entrepreneur with experience in the software, healthcare, and CPG industries. He continues to maintain his passion for technology as an active angel investor with a focus on b2b, consumer saas and health tech. Rasool maintains an active role with CEO’s as a board member, mentor and advisor. He currently serves on the boards ofthe Victoria Foundation, VIATEC, and Checkfront Software.

Investment focus

SaaS, Content, Cloud Computing
Seed, Angel, Pre-Seed
Canada, United States

Portfolio highlights

Outway — Inspiring personal bests.
Defined — Real-time token prices, charts, wallet tracking & trading terminal for Solana, Ethereum, Base, Arbitrum, Sui, BSC, Tron & many more networks
Cognito Health — Canada's only integrated online mental health solution. Accessible and affordable treatment for your mental health. Book a free initial assessment today.

Serial Entrepreneur and Investor in Internet Businesses and Marketplaces | Board Professional | Co-Founder at DealGuru and Bonusway

Investment focus

Marketplace, Restaurants, Software
Angel, Funding Round, Seed
Finland, Canada, Sweden

Portfolio highlights

DealGuru — DealGuru is a stealth startup in a ecommerce space.
Serviceform — Welcome to future of communication - the truly all-in-one conversion and management software built for established businesses. Start now!
Fiksuvuokraus.fi — Fiksuvuokraus.fi is an apartment renting platform for long-term contracts. In our service, the rental process is simplified and accelerated with the latest technologies that are primarily used only for apartment selling. We think that also rental apartments deserve to be found with modern tools.

Mikko has 10+ years of experience from managing high-growth online businesses, including that of website platform Kotisivukone.fi, sold to Fonecta in January 2013.

Investment focus

SaaS, Travel, Software
Seed, Angel
Canada

Portfolio highlights

Hostaway — Hostaway Vacation Rental Software and Airbnb Management System Helps You Grow Your Vacation Rental Property Management Business By Automating And Streamlining Every Aspect Of Your Business across Airbnb, Vrbo, Booking.com, Expedia, and many more.

Stephen Curry currently works as the Founder and Partner at Unanimous Media. He previously worked at Slyce.io as co-founder. Stephen Curry attended Davidson College in 2006.

Investment focus

Mobile, E-Commerce, Mobile Apps
Series A, Series C, Series B
United States, Canada, Portugal

Portfolio highlights

Step — Step Mobile offers the best secured credit card to build credit. No credit check, cashback on every purchase, and average score increase of 57 points.
Super.com — Through rich rewards and everyday savings, Super helps you access more of what you want at better prices, escape overspending, and level up life.
TMRW Sports — TMRW Sports is harnessing technology to build modern approaches to sports, media, and entertainment.

Stuart MacDonald is a Venture Advisor of Narrative.Fund.

Investment focus

Software, SaaS, Travel
Seed, Funding Round
Canada

Portfolio highlights

Sherpa° — eVisas and travel requirements information for every step of your customer journey.
Swept — Swept is a tech company that develop software solutions for the janitorial industry. Swept was founded by Matt Cooper and Michael Brown in August 2014 and is based in Nova Scotia.

Andrew Kitchell is a Founder and Chief Executive Officer at Lyric and Wheelhouse. He is a former CEO & Founder at Beyond Pricing and Founder, Product Design at 30 Words. Mr. Kitchell studied at Duke University.

Investment focus

Software, Vacation Rental, SaaS
Seed
Canada, United States

Portfolio highlights

Topkey — Topkey is an app that tracks expenses by property, sync transactions across systems, and save tons of money on bookkeeping. Topkey was founded in 2020 and was headquartered in San Francisco, USA.
Enso Connect — Seamless digital guest experience from booking through the entire stay and long-lasting relationships after check-out. Vacation rentals & Hotels remarketing tool.

Jeffery Boyd currently works as the founder and managing director for Brothers Brook, LLC. He previously worked at Booking Holdings Inc., formerly The Priceline Group Inc as the Chairman. Jeffery attended Cornell Law School.

Investment focus

Travel, Health Care, E-Commerce
Series A, Funding Round, Series B
United States, Canada

Portfolio highlights

Plannin — Plannin is a travel booking platform that offers travelers tools and resources.
@hotel — Tripscout is the center of the world for passionate travelers. We bring you the best articles and videos to satisfy your wanderlust and help you plan amazing trips.
Cruisebound — Cruising made simple. Cruisebound makes it easy to book your cruise online. Compare cruises from major cruise lines and find the best fit for your vacation needs.

Andrew Wilkinson is the Co-Founder of Tiny. He attended Ryerson University.

Investment focus

Software, Internet, SaaS
Seed, Series A, Pre-Seed
Canada, United States, Germany

Portfolio highlights

Practice — Sell your expertise online, and manage your business, all in one place.
Cognito Health — Canada's only integrated online mental health solution. Accessible and affordable treatment for your mental health. Book a free initial assessment today.
Windsor.io — Windsor lets sales and marketing teams improve conversion with personal videos. Record a single video, hook up your CRM and hit send. Our AI will create and send a personal video to every recipient

Michael Hyatt is the Executive Chairman and Co-Founder of BlueCat Networks and a recipient of the Top 40 Under 40™ Award. BlueCat is a four-time winner of “Deloitte’s Fast 50” and has received Gartner’s highest “Strong Positive” rating. Michael also co-founded Dyadem, a highly successful software company that was acquired by IHS (NYSE: IHS).Michael is a weekly business commentator on CBC Newsworld and has been featured on the cover of Canadian Business Magazine. He is also a finalist in Ernst & Young’s Entrepreneur of the Year Award and an active participant and lender for three special charities: Kiva.org, OneProsper and Future Possibilities for Kids.

Investment focus

Software, SaaS, Accounting
Seed, Series A, Funding Round
Canada, United States

Portfolio highlights

MinuteBox — Secure legal entity management in the cloud. Minute books, transactions, compliance, document assembly, cap tables, e-signature, automated workflows
Enso Connect — Seamless digital guest experience from booking through the entire stay and long-lasting relationships after check-out. Vacation rentals & Hotels remarketing tool.
GoBolt — Elevate your logistics game while reducing your carbon footprint with GoBolt, your trusted 3PL provider focused on sustainability.

Neil Wainwright is the Founder and CEO of UpHabit.

Investment focus

Travel, Leisure, Podcast
Seed, Angel
Canada, United States

Portfolio highlights

Wishroute — Gain, retain and engage customers with conversational text messaging built for wellness apps, products and services. We do the 2-way texting for you and will help you optimize user experiences to increase revenue, engagement, conversion rates, activation rates, retention and more.
LumiQ — LumiQ makes earning CPD hours fun and accessible for individual accounting professionals and teams on-the-go. Get started now!
Pilot — Social Trip Planner that makes building an itinerary with friends easy. Easily plan trips, and see where friends have been so you can go too.

Steven Myhill-Jones

Investment focus

SaaS, Mobile, Travel
Seed
Canada

Portfolio highlights

Kiind.me — Buy, send and track digital gift cards for your reward and incentive programs.
Checkfront — With over 4000 customers in 120 countries, Checkfront is an Built on the _Saas_ model, Checkfront is a fully managed solution. It includes automated updates, backups, and industry-leading security on a high speed, highavailability network.

LP Maurice is the CEO & Co-founder of Busbud, an e-commerce startup focused on intercity bus travel that makes it easy to book bus tickets in 80+ countries. Busbud was named one of the 3 most innovative companies in Canada in 2014 according to PwC. LP holds an MBA from Harvard University, a Master’s degree in Corporate Law from theUniversity of Montreal and a Bachelor’s degree in Finance from HEC Montreal.

Investment focus

Travel, Tourism, Software
Series A
Canada

Portfolio highlights

Sherpa° — eVisas and travel requirements information for every step of your customer journey.

Entrepreneur, investor.

Investment focus

Software, Accounting, E-Commerce
Seed, Pre-Seed, Series A
Canada, United Kingdom

Portfolio highlights

Connect4 — The client-centric platform for you and your team. Consistently deliver outstanding client meetings. Every single time.
E-State Planner — Cloud-based estate planning software - for lawyers by lawyers. Save time, reduce malpractice errors, and improve your service delivery.
Float Financial — All-in-one corporate cards, fast bill payments, reimbursements, and expense management software. Get started today for free.

Jimmy G.

Investment focus

Travel, Information Technology
Pre-Seed
Canada

Portfolio highlights

instaHop — We inspire you to craft personal travel plans... and create unforgettable experiences. Adventure awaits - lets make it happen!

Lauri Sommarbergis the Co-Founder and Board Member of LVS Brokers.

Investment focus

SaaS, Travel, Software
Seed
Canada

Portfolio highlights

Hostaway — Hostaway Vacation Rental Software and Airbnb Management System Helps You Grow Your Vacation Rental Property Management Business By Automating And Streamlining Every Aspect Of Your Business across Airbnb, Vrbo, Booking.com, Expedia, and many more.

David Arnsdorf - Co-Founder & Managing Partner @ Pomme Natural Markets

Investment focus

SaaS, Cloud Computing, Marketing
Seed, Angel, Funding Round
Canada, United States

Portfolio highlights

Checkfront — With over 4000 customers in 120 countries, Checkfront is an Built on the _Saas_ model, Checkfront is a fully managed solution. It includes automated updates, backups, and industry-leading security on a high speed, highavailability network.
Social Nature — Free Organic Product Samples & Shopping Reviews - Social Nature
Shadow Networks — Get this domain name before someone else does. Quick and painless shopping. Affordable payment options available.

Rajiv Khaneja is the Founder at AdButler

Investment focus

SaaS, Mobile, Travel
Seed
Canada

Portfolio highlights

Outway — Inspiring personal bests.
Checkfront — With over 4000 customers in 120 countries, Checkfront is an Built on the _Saas_ model, Checkfront is a fully managed solution. It includes automated updates, backups, and industry-leading security on a high speed, highavailability network.

Mike Liverton

Investment focus

SaaS, Travel, Software
Pre-Seed
Canada

Portfolio highlights

Enso Connect — Seamless digital guest experience from booking through the entire stay and long-lasting relationships after check-out. Vacation rentals & Hotels remarketing tool.

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