Everything still depends on you.
How do you change the way the company runs without becoming the bottleneck—or losing touch with what matters?
For founders & founding teams
When everyone
looks to you,
who do you turn to?
Confidential, practical advice for founders navigating growth, team tensions, and consequential decisions.
Former CMO, Expedia.comFormer CRO & CMO, FreshBooks
Founder, Expedia.caInvestorBoard Member
You don’t have to carry every question alone.
For founders and founding teams running a business and making decisions about customers, growth, people, and their own role. Do any of these sound familiar?
Your founding team is pulling in different directions.
How do you address differences in priorities, roles, or expectations before they hold the business back?
Growth has stalled—or created a new set of problems.
Who should you serve first, what do customers actually value, and is your positioning or pricing holding you back?
You need to say the difficult thing out loud.
A concern about a key person. Pressure from investors. Doubts about a decision—or your own role. Somewhere to work through it without having to project certainty.
About Stuart
I understand the weight of leading a business.
I started Expedia.ca from my home, recruited the team, and built the business. Later, as CMO of Expedia.com and CRO & CMO of FreshBooks, I led growth and teams through change, including helping reshape FreshBooks’ business model and organization.
For more than 20 years, I’ve advised founders and executives at dozens of companies worldwide and supported businesses as an investor and board member. Most recently, I stepped in on an interim basis to lead the commercial function of a technical equipment company and to serve as CMO of a vertical AI company.
Recent operating and advisory work keeps me close to changing markets, buyers, and teams—including how AI is reshaping go-to-market. I bring that perspective to our conversations: challenging assumptions and spotting pitfalls before you commit.
Where I’m most useful
- Customers & positioningIdeal customer · Value proposition · Pricing
- Go-to-marketGrowth strategy · Channels · Brand
- Marketing leadershipFirst marketing hire · Team design · Agency vs. in-house
Experience across different business models
- TechnologyAI · IoT · B2B SaaS · Crypto
- ConsumereCommerce · Loyalty
- TravelAviation · Accommodations · Ancillaries · Packages
Client perspectives
In founders’ words.
“Stuart helped us break through a growth plateau by getting much clearer about who we should serve, what those customers truly valued, and where we should focus. That clarity gave us the confidence to say no to the wrong opportunities and build a more focused, profitable business.”
Anubhav · Founder and CEO · AI SaaS
“Stuart has helped me navigate building and scaling a brand that’s now on track for eight figures in annual revenue as we expand across the US. His kindness, empathy and genuine passion for helping founders are second to none. His guidance has made a real difference.
He’s an absolute weapon, a great guy, and someone you want in your corner.”
Ben · Founder and CEO · Crypto
Choose your advisory session.
Private video advice for the decision in front of you, with no commitment to ongoing support. Co‑founders are welcome to join the same session.
Recommended to start
60 minutes
USD$450
Work through a consequential decision.
Bring one significant decision or a connected set of challenges. We’ll examine the assumptions, weigh the trade-offs, and identify the next actions worth taking.
Reserve 60 minutesChoose a time and pay securely to confirm your booking.
For a focused question or follow-up
30 minutes
USD$250
Move one focused question forward.
Bring one specific question or a follow-up from an earlier session. We’ll test your thinking, compare the options, and identify your next step.
Reserve 30 minutesChoose a time and pay securely to confirm your booking.
First-session guarantee. If your first session isn’t useful, email me by 11:59 p.m. Eastern Time the day after your session for a full refund. Continue into ongoing advisory within 60 days and the fee is credited toward it. How this works
Prices in USD, plus taxes as appropriate
24-hour cancellation & rescheduling noticeAlready booked? Need to make a change?
Use the confirmation email from Cal.com to reschedule or cancel. For booking or payment questions, email bookings@stuartmacdonald.ca.
Unsure which session fits? Email a few sentences about your situation. Booking or payment questions: bookings@stuartmacdonald.ca.
Your first advisory session
Bring the situation.
We’ll work through it together.
Before we meet
A few sentences about your company, its stage, and what’s on your mind will help us get started. No deck or polished brief is required.
During the session
We’ll meet by video: understand the situation, challenge the assumptions and options, then identify practical next actions. Bring a growth plateau, a positioning or pricing question, your first marketing hire, changing founder roles, or a key team challenge. You don’t need to know exactly what to ask.
Afterward
You decide whether another session would help. If you want ongoing support, we can discuss the scope and rhythm that fits you.
How does confidentiality work?
Your sessions are confidential. When a company or investor sponsors the work, we agree before starting on who the client is, what remains confidential, and what, if anything, is shared with the sponsor.
Can I cancel or reschedule?
With at least 24 hours’ notice, you can cancel for a refund or reschedule your session. Email bookings@stuartmacdonald.ca to change your booking.
Cancellations with less than 24 hours’ notice and missed sessions are non-refundable. This includes sessions booked less than 24 hours in advance. Exceptions may be made at Stuart’s discretion.
What if the session isn’t useful?
If your first session isn’t useful, email me by 11:59 p.m. Eastern Time the day after your session and I’ll refund it in full, no questions asked. Email bookings@stuartmacdonald.ca. This applies to your first session, whether 30 or 60 minutes.
The guarantee covers sessions that take place. Cancellations and missed sessions follow the cancellation policy above.
If we start an ongoing advisory engagement within 60 days of your first session, that session’s fee is credited toward it.
Is this suitable for me or my company?
This is for founders and founding teams running a business and facing growth, customer, team, or leadership decisions. My experience spans technology, commerce, and travel, with particular depth in customers, positioning, and growth. Bring a decision you want to examine, even if the problem is not yet neatly defined. If you’re unsure whether I’m the right fit, get in touch with a little context about your company and what you’re facing.
Ongoing advisory
Someone you can
come back to.
An ongoing relationship gives you a regular place to test your thinking, work through difficult decisions, and revisit what’s working as your company—and your role—evolves.
Work with me individually or as a founding team. We usually meet weekly, with flexibility around your needs. Before starting, we’ll agree on the priorities, scope, fees, and any support between sessions. Use our conversations to test a decision, work through a difficult discussion, and revisit what changed after you acted. Ongoing advisory isn’t an operating role: I help you make better decisions rather than running your marketing for you.
Referrals and investor introductions are welcome, including engagements sponsored by your company or an investor. How confidentiality works
“Stuart has been on our board since 2018 and is as useful between meetings as in them. He combines operating experience with a sharp feel for customers, positioning, and growth, helping us spot weaknesses early and avoid decisions that would have boxed us in.”
Max · Co-founder and CEO · Airline Ancillaries
No charge. We’ll talk through what you need and whether ongoing advisory is the right fit.
Let’s talk
What are you working through?
Bring the decision, the context, and the questions you cannot easily discuss elsewhere.