Identity fused with the company
When the line between how the business is doing and how you are doing has quietly disappeared.
For the ones building something
Therapy for founders and entrepreneurs
Running a company means the buck stops with you, always. The wins are yours and so is everything that goes wrong, and there is rarely anyone you can be fully honest with, not your team, not your investors, often not even the people at home. You learned to carry the uncertainty, the pressure, the loneliness of it, because carrying it is the job.
But founders pay a private tax for that. The always-on vigilance, the identity fused completely with the company, the sense that if you stop pushing it all falls apart. It can leave you successful and depleted at the same time, and unsure who you would even be if you slowed down.
I work with founders and entrepreneurs who need one place where they do not have to perform, where they can say the real thing without it becoming a leadership problem or a fundraising risk. Before I became a therapist I spent years in finance and senior leadership, so the world you are in is not foreign to me.
This is not coaching and it is not strategy. It is a space to put down what you have been carrying and think clearly about your own life, not just the company's. If that sounds useful, the first step is a free 15-minute call.
Fifteen minutes, private, no obligation.
Jordan Wiener
Registered Psychotherapist (Qualifying), MA
CRPO #21656
Background in finance and as a chief of staff. Online across Ontario.
There is rarely anyone you can be fully honest with, not your team, not your investors, often not even the people at home.
What we might work on
The loneliness at the top
Being the one everyone looks to, with no one you can be completely honest with about the hard parts.
The weight behind the payroll
Carrying the livelihoods of the people who work for you, and everything riding on your next decision.
Never being able to switch off
A mind that stays on the company at dinner, on weekends, at 3am, because it never really stops.
Common questions
Do founders and entrepreneurs actually go to therapy?
More than it looks like, they just tend not to talk about it. Running a company is uniquely isolating, and a lot of founders reach a point where they need one place to be honest that has nothing to do with their team, their board, or their investors. Wanting that is not a weakness. It is usually a sign of someone carrying a great deal and wanting to keep doing it well.
Is this therapy or is it coaching?
It is therapy. Coaching is generally about performance and strategy. This is about you, the person underneath the company, the pressure you carry, the toll it takes, and what you actually want your life to look like. Some founders have a coach and a therapist for different reasons. If what you need is a confidential space to work through what you are carrying, that is what this is.
Will you actually understand the world I operate in?
I spent years in finance and senior leadership before I trained as a therapist, so the pressure, the stakes, and the loneliness of being the one everyone looks to are not abstract to me. You should not have to spend the first month explaining your world before we can get to what matters.
Is it completely confidential and separate from my company?
Yes. This is private therapy with no connection to your company, your board, your investors, or anyone in your professional world. What you talk about stays between us. For a lot of founders, that separation is exactly what makes it possible to be honest.
I barely have time to breathe. How does this fit a founder's schedule?
Sessions are online across Ontario, so there is no commute and it fits into a working week. The first step is just a free 15-minute call to see whether it is worth your time. Most founders find that one hour of not carrying it alone gives back more than it costs.
How do sessions fit around an unpredictable week?
Sessions are online across Ontario, so there is no commute and they fit into a working week more easily than in-person would. We find a regular time that works for you, and if your schedule is genuinely unpredictable we can talk about how to handle that. The first step is a free 15-minute call.
What does it cost, and is it covered?
Individual sessions are $160 for a 50-minute session. Whether therapy is covered depends on your specific plan. Some extended-health plans include a Registered Psychotherapist and some do not, so the best step is to check your own policy for what it covers. You will receive a receipt you can submit if your plan allows it. If cost is a concern, it is worth raising on the free call.
Do I have to be in crisis to book?
No. Most of the founders I work with are functioning well, still building, still dependable, and just quietly more depleted or more on-edge than they used to be. You do not need a crisis or a diagnosis to deserve support. If something has been sitting with you, that is reason enough.
This is one part of my work with men under pressure. Related reading: when you are what you do and high-functioning and running on empty.
Jordan Wiener, MA, is a Registered Psychotherapist (Qualifying), CRPO #21656, offering online therapy for men in Toronto and across Ontario. This page is educational and is not a substitute for individual care.