July 7, 2023: What leads to a large round?

What does this mean?

Another two-for-one special with news and announcements. So, what are the announcements?

• Rose Rocket raised $38m USD Series B for its transportation management software. It provides a SAAS solution that provides a communication and coordination operating system for truck fleets.

• Passage, a super app helping people relocate to Canada, raised a $40m pre-seed round led by Drive Capital.

How did these companies get to raise such large rounds?

Very different paths for both:

Rose Rocket was founded in 2016 and has slowly built a system for recording whose growth is fuelled by network effects and multiple revenue streams. It laid the foundation over the years and it is now evident that it can grow into a massive business.

What does this mean for those who might now know?

Ok system of record, means it is the primary source of truth for mission-critical data for trucking companies. This makes it very sticky and hard to stop using it.

Network effect: when one trucking company uses it the value of Rose Rocket improves for all users.

Multiple revenue streams: as they grow in importance they can go from a pure SAAS business to one that charges for additional services like processing payments.

Thanks, now how did Passage raise such a large round

Based on the founder's reputation and experience. Passage is more of a concept than a business now but Martin Basiri founded ApplyBoard an edtech company that helps foreign students find post-secondary education. That company scaled rapidly and is valued at $3b+. Martin left ApplyBoard to start Passage which is helping skilled foreign workers relocate to Canada (or other countries) where they can earn more.

If you looked at the investors in Passage many of them are ones that were early investors in ApplyBoard. Why is this?

• Martin has made them money already and they believe he can do it again. This is partially a reward and partially a belief.

• Passage is adjacent to ApplyBoard so the skill and knowledge is transferable.

• This is a larger opportunity than ApplyBoard as there are more people in the market and they need help from multiple angles to relocate including financing

What do these two deals have in common?

On the top level, solve large problems in large markets. Less obvious is using technology to reduce search and transaction costs and using that to build flywheels in your product.

Takeaway for the community?

Money is out there for bold ideas that have moats and teams that can execute even if AI is not your main value proposition.

Both these companies are improving the availability and transparency of data which reduces the search and transaction costs for the underlying action. RoseRocket allows fleet managers to know where a truck is while Passage provides potential immigrants with information on how to move to Canada and finance that transaction. Another underrated part of both companies is that their business models have multiple revenue streams enabling them to be nimble in how they derive value from the services they provide.

RoseRocket is a reminder that great companies take a long time to build.

Listen to the most recent episode of Quick Takes

Alex Norman here. I have used a virtual EA for years. Double, a TechTO partner, asked me to share some of my experience. Between running TechTO and my fund, N49P, it is nearly impossible for me to stay on top of every task. I would feel terrible every time I let a follow-up slip or did not get to a Founder’s email. Also, all the context-switching was driving me crazy and burning me out. After spending the time to get a virtual EA up to speed, I have found it streamlines everything about my day. It lets me focus on what is most important to me and helps me delegate what isn’t.

Double was founded in 2018 by a team of leaders from Sunrise Calendar, Microsoft, & Front. They know productivity and how people collaborate. They built Double with these experiences in mind. Double stands out against other EA offerings through:

Quality: Their career EAs have on average 7 years of experience supporting C-suite executives. They are North-America based, though Double does have France-based EAs to support French-speaking Canadian execs and execs in France. Double EAs are continuously trained on new tools, skills, and industries, and they have access to various productivity tools and training to bolster their efficacy even further. While you have your own dedicated EA through Double, they are supported by a wider, vibrant EA community to borrow on each other’s expertise.

Flexibility & Transparency: Contracts start at 10 hours per month and you can scale up and down as much as you'd like: e.g. if one month you need 20 hours/week because its fundraising time and another month you need 3 hours/week because you're off traveling - that's totally fine. Pricing is transparent & available on their website without any need to sign up first to estimate costs. There are no hidden fees and you just pay a monthly subscription for the hours you want, and an hourly fee for any hour you go above (if you do). You get a super-detailed breakdown of everything your EA worked on and are only billed by the minute for each task (e.g. 2 min to reschedule a meeting).

Speed and ease of delegation: Rather than spending weeks recruiting help yourself - they do all the heavy lifting. You can start delegating to a hand-picked EA within a week of signing up. Double makes it really easy to delegate, especially for first-time delegators, as they have detailed templates you can just fill in to delegate common tasks. Double also has a suite of proprietary delegation tools that make it super simple to delegate, e.g. Chrome extensions that turn whatever you're looking at (e.g. flight ticket) into a task for your EA.

Schedule a call here

*this is sponsored content

Another episode of Founders Journey just dropped! Make sure you like and subscribe wherever you are listening

How to make it easy for your VC to walk you in the door of potential customers

It’s not always about where your VC can help, but sometimes more about where they CAN’T

Learn about the 7 different archetypes of tech entrepreneurs. Which one are you?

Senior Software Engineer, Rose Rocket (Toronto, ON)

Why is this cool? Rose Rocket is a market leader in Transportation Management Software. They’re a startup going after the $700+ billion dollar trucking industry, leading the shift to SaaS while revolutionizing the way trucking companies sell, service, and innovate. In this role, you will drive massive growth, help large customers succeed, build workflows, data models, and features to support the product (and more).

*Reply to this email and let us know the jobs you'd like to see

• TechTO: Together | July 10, 2023: TechTO: Together returns with another outstanding line-up of speakers, great networking, and the famous afterparty you love!

• Startup Fest | July 12 - 15, 2023: Get a 15% discount here

• TechTO: Montreal | July 13, 2023: We’re back in Montreal to kick off Startup Fest. Will you be there? It’s the perfect after-party for any of your Startup Fest events.

• Product4Good Conference | October 18, 2023: Explore the future of Product Management and give back to the community

Want to showcase your company, events, and opportunities to 60,000+ subscribers across the Canadian Tech Eco-system? Reach out to [email protected] to learn more