I am the founder and CEO at My Wellbeing, where we take the stress out of finding the right therapist for you through personalized matchmaking, community building, and curated content.


“Test everything,” I heard for about the 100th time last summer as I sat cross-legged at my desk, listening to Frank Rimalovski, Executive Director of the NYU Entrepreneurial Institute, introduce one of our invaluable guest speakers during an “Ask Me Anything” session for our Summer Launchpad Program cohort in 2017.


Pen-in-hand, I drew a box around the word test.


Since day one of My Wellbeing, I cannot count the number of blog posts I read, lectures I attended, podcasts I listened to, books I notated, and advisors I talked to about the importance of testing hypotheses before investing any unnecessary time or money into your startup’s next initiative. Particularly the most vulnerable ones: the hypotheses that may bring an end to your business if you are wrong.


And yet, I am an entrepreneur, which implies both that I am eager to solve the world’s hardest problems and that I have limited patience.


For example, when therapy-seekers or therapists share a problem they are experiencing, I want to fix it, and I want to fix it fast. If unchecked, this good intention can lead to leaping too soon into the solution before really testing the most efficient and effective way to solve the problem at hand.


I recently attended Frank’s book launch with his writing partner Giff Constable, who both released Testing With Humans, the chapter two to their first literary success, Talking with Humans. Safe to say they are both experts on the topic of learning your customers’ problems and designing tests to discover the most efficient, effective ways of solving them.


While discussing the importance of testing, Giff asked the room a rhetorical question:

“How can I learn just as much, if not more, with half the time and effort?”


This could not be a more valuable mantra to keep top of mind, especially for entrepreneurs. Along these lines, I’m happy to share an example of when I lost sight of this and how my team and I re-corrected before it was too late.

Our mistake: “We know how to fix this.”

Finding a therapist on your own is extremely challenging. If you’ve made it past the hurdle of making contact with a human, it’s sometimes even harder to know if that person is the right fit for you.


Our mission as a company is to take away the stress of connecting with a compatible therapist, and to improve the experience of therapy from start to finish. Our process works as such: someone looking for a therapist comes to our website and completes a brief questionnaire through which they share their therapist preferences. We then send them 1-3 personalized matches to their inbox.


The person looking for a therapist then goes to the therapist’s scheduling page or website and decides to book a free phone consultation, to book an appointment, to ask My Wellbeing for another match, or to do none of those things and move on.


In our experience, we learned that some of the therapists we are working with do not have high quality web presence. We found that therapy-seekers who may be a very good fit for a particular therapist’s style of work and experience were often dissuaded from scheduling with their therapist match because their therapist’s web presence was unattractive, discouraging or misleading.



  • The problem: Therapy-seekers feel dissuaded to follow through with their therapist match.
  • The hypothesis: Therapy-seekers would be significantly more likely to follow through with their therapist match if their match had stronger web presence.


Where did my mind jump?

  • The answer: Fix their web presence, as quickly and as beautifully as possible.


The next thing I did was to brainstorm with my team a list of questions that I and my team thought both deserved to be on that page, and would help the therapy-seeker learn more about their therapist, to ultimately help them book their first appointment.


We outlined a Q&A that -- from our clinical and marketing expertise -- made the most sense to us. We put about 25 questions in a Google Doc and shared the document with 100 of our therapists, asking for them to complete and return their answers to us within 2 weeks. We would use this content to build personalized web pages for the therapists we work with, which we would share with the therapy-seekers when they matched with a particular therapist.


What did we find?


Therapists were largely overwhelmed by the length and depth of this task. Moreover, they had some questions about why we chose these specific questions.


The worst part?


We didn’t have concrete, data-backed answers. Why were we building web presence? Why did we choose these particular questions? Our team thought they’d be helpful. The bottom line is that answer is not strong enough.

Our lesson: “What do you think?”

We realized quite quickly we had lost sight of “test everything.”


We assumed therapy-seekers wanted better therapist web presence. We assumed we knew which questions to ask. We assumed our therapists would agree and that these questions would actually be helpful for our therapy-seekers when choosing whether or not to move forward with any given therapist.


What didn’t we do? Ask.


As quickly as we had made the original decision to leap forward, we made the decision to pause and to ask.


We called about 100 of our most recent therapy-seekers to learn if better web presence would be helpful, and we guessed right: it would.


We put all 25 questions into a Typeform with binary yes/no answer options. We sent the Typeform to our community, asking each survey-ee to respond “Yes” if they believed the question would be helpful when choosing a therapist, and “No” if they’d rather cut it and save their headspace and time. We included a blank fill-in question to learn if there were any helpful questions we’d missed entirely.


Within hours, we learned which questions were most necessary and we accrued black-and-white data that we would share with our therapists to explain:


  1. Why we were making these pages
  2. Why we would include certain questions, and
  3. How important those questions and answers are to prospective clients of theirs.


Our unfortunate loss here is that the therapists we work with, who we deeply value, have invested time and energy into questions that may ultimately be cut.


Our work is to explain transparently what happened and why, and to remind them how much we value their time and perspective. Behaviorally, we have suggested the opposite by wasting their time. Now we must make up for that.


You can imagine how much better this experience would have been for all parties involved had we collected our therapy-seeker-facing data before requesting that our therapists complete the Q&As.

How to test moving forward

  1. Ask the people you are trying to help


As a social worker, I generally refrain from using words like “always” and “never.”


Accordingly, I won’t tell you to always test before you move forward. One of the hardest things about being a founder is to practice judgement around when a decision or initiative is important enough that you need to invest the time and energy into testing it. There will be 100s of decisions a day, and many of them you will need to decide quickly in order to maintain the pace and integrity of your new, budding company.*


*If you need more support learning which decisions to test and why, in addition to Testing with Humans, The Effective Executive is a great book about setting up rules and processes. Ideally, you base all of your decisions on results of experiments, and then you design processes that follow the logic of the learning you have already tested. In this way, you are scaling the impact of each individual experiment.


Rather than “never” or “always,” I urge you to whenever possible, ask the people you are trying to help, and ask them first.


You will gain invaluable insight and perspective that you may otherwise be blind to, not because you are a bad person, a failure, or you don’t have founder/market fit, but because you are balancing about 800 roles in one person, you are human, and you will miss something.


Your may also receive feedback that unanimously supports your original idea. Your instinct may be to think, “Ah, I wasted time on that experiment. I didn’t need to test it, I knew all along.” This would be flawed thinking. You now have earned confidence. Post-experiment, you know for sure, with data behind you, that it’s time to invest your limited time and resources into that particular solution to a problem.


Note: be sure to ask the people you specifically are hoping to help. If you are running a company that is supporting or serving people over the age of 65 and you test with people under the age of 20, you will collect flawed data.


What is the problem?


I can say with empathy and experience that it is relatively easy to design an experiment that is testing for at least 5 things at the same time. This is because you likely have a lot of ideas, and you, again, may be very eager to start acting on them.


I urge you not to do this. Instead, distill as much as possible that you are testing to learn one very specific thing per experiment.


You can be running multiple experiments at the same time, but each hypothesis ought to be tested in its own experiment. Otherwise, if one hypothesis is correct and another is wrong, but both are being tested in the same experiment, the conclusion of one or the other may throw you off and you may miss valuable data.


How can you learn just as much, if not more, with half the time and effort?


Say you designed an experiment that would give 100% confidence in your answer. Now imagine that experiment will take about 4 weeks and about $10,000 to complete.


Is there an alternative that will give you at least 75% confidence you’re moving in the right direction, while also empowering you to save time, money, and team energy?


It’s possible your first idea is the fastest, cheapest experiment you can design, particularly if you’re not running a software or consumer-facing company. It’s also possible that there is a faster and cheaper way to learn what you need to know.


There are no black-and-white answers here. I suggest to at minimum ask yourself the question.


Note: If you notice that you repeatedly forget to remind yourself to test or distill, recruit one of your teammates to hold you accountable.


How will you improve your next experiment?


As you begin and continue running experiments, you will learn the things that work especially well for you, your team, your industry, your users, and your market. Take note of that.


You will also learn a series of things that flop or fail. This is inevitable. Take note of that, too.


Along the way, be sure to integrate what you’re learning into your future experiments. Like a machine learning algorithm, you will get better over time the more data you accrue.




I hope the above, and sharing a bit about how I am definitely always learning, is helpful for you.


If you have further questions about me or My Wellbeing, keep in touch: mywellbeing.com and @findmywellbeing.