Interview: Building an anti-regret machine with Tyler Bryden

Reading time: 13 minutes

Many people take lots of notes but then don’t know what to do with them. Our notes, whether written, audio, or video, are a treasure trove of insights about ourselves, but it can be hard to extract those insights. That’s why I was incredibly excited when I discovered Speak Ai, a company on a mission to help people capture, analyze and share media to improve their wellbeing and productivity. Speak Ai allows users to create text notes, record audio notes, capture and import video, and then automatically get valuable insights from their entries.

I spoke with Tyler Bryden, the CEO of Speak Ai, about the company’s mission and his own personal journey. Tyler is an ex-competitive hockey player and a mental health advocate. He has a particular interest in psychedelics and the quantified self movement. His passion for helping people live happier and healthier lives has led him to work on Speak Ai.

In this interview, we talked about the relationship between wellbeing and productivity, the quantified self, how to build an anti-regret machine, how to make self-reflection frictionless, the two types of communication, the future of Speak Ai, and more. Enjoy the read!

Hi Tyler! Thanks so much for agreeing to this interview. I have so many things I want to ask you, but I’m going to start with a general one. What do you think is the relationship between productivity and wellbeing?

Someone I know defines productivity as moving towards a personal goal. So one of the things that becomes really interesting is how could we measure productivity? Some people look at the length or duration, especially with note taking or audio recordings, such as how many words you wrote or how many notes you created, but that doesn’t necessarily mean that you were productive or working towards a goal. Maybe there were only three sentences that mattered. How do you quantify and measure that? Let me show you a chart.

These are of course very rudimentary definitions, but there is a baseline where we operate if we’re lucky. Many of us can operate at that baseline, but many have past trauma that doesn’t necessarily allow us to operate at a baseline. Then, at rock bottom, you are in a crisis situation, whether it’s inpatient experience in the hospital or a suicide attempt. We lose a lot of people here, especially if they don’t have the love and the support that they actually need. And then, at the very top is full potential. Full potential is such a subjective measure of what we actually are and who we actually are. But the idea is almost that none of us can actually reach it. It’s this transcendent state where we’re in flow for fourteen hours a day. You feel untouchable, nothing can stop you. And, and that’s something that I’m really trying to figure out and discover.

Many of us are trying to optimize around professional success, and that’s our measure of our full potential. For others, we’re trying to optimize for intimate relationships that we have in our life, our relationships with family and friends. Either way, we need to go through a reflective mechanism.

It reminds me of the eighty-year study and where they asked people: what do you regret at the end of the life? And much of it was “I wish I didn’t work so much”, “I wish I’d spent more time with family and friends.” So how, can we build an anti-regret machine? I went a little bit on a tangent there, but I think these are the challenges with trying to define productivity and wellbeing, because it’s so subjective to who we actually are.

That’s true. Looking at this graph, do you think wellbeing and productivity can actually be measured?

Many of us have fallen into this pressure before. If we’re not operating at a high pace, constantly churning out output to hit these metrics, we feel like we’re not actually being successful in terms of productivity. Many of us have had an experience of a breakdown or a burnout where we’ve realized that in order to actually be productive and effective, you actually deeply need to take care of your wellbeing and your mental health. That’s why having an indicator that you’re on a path to burnout may be helpful. This way, when you start to feel that stress or pressure, you can drop the other things and just take care of yourself. That’s true productivity and effectiveness. It’s actually going to get you faster towards the goals, instead of trying to power through, then burn out and not even accomplish what you were actually trying to accomplish. So, it’s hard to measure, but some of the most successful people have a balanced relationship between productivity and wellbeing. 

That sounds like qualitative measurement, which may feel intuitive to quite a few people, but there’s this more extreme version of measuring productivity which has been popular. What do you think about the quantified self movement? 

Statistically speaking, when we at least try to measure something, even if it’s a subjective measure, it helps us. If you’re monitoring your financial income, you’re going to be more mindful with money. You’re not going to spend as much. So just the act of trying to measure something then puts you in that conscious state to at least try to improve on that.

Let me show you another chart, where I go as deep into my quantified self as I can actually go and, and then try to build categories and see if there’s any correlation.

Check out the full interactive chart.

I had a significant breakdown when I was at 21. Before that, my self-confidence was at an all time high. It was grandiose. But then, I had my first psychedelic experiences and I didn’t know about integration. I didn’t know about the power of these substances. And all of this stuff started to combine to create a massive drop in my mental health and wellbeing.

I think the quantified self is beautiful. Again, there are so many subjective measures and it’s really hard to do this objectively. But the self-reflective act and trying to measure it is a powerful activity.

I’m impressed by the number of categories you track. That sounds like a lot of work.

Yes. It’s not very fun to just fill input fields. That’s why it’s important to be able to do that through unstructured creation, like expressive journaling. The one that I’m big into is audio. I love to record audio notes. The idea is to remove myself and let myself become a vessel and a channel. Then free associations reveal things about myself that I can extract and reflect upon. I’m trying to make that self-reflection and the measurement process as enjoyable and seamless as possible so that you can actually continue doing it.

There’s no point, I guess, in collecting all of this data if you don’t understand it and if you never look at it again. Is that partly what inspired you to start working on Speak Ai?

That’s correct. A lot of people suffered or had a difficult experience which forced them to learn. But there’s nothing worse than seeing someone have to go through pain that they don’t need to go through. Because of childhood trauma and my struggle with my own sexuality and who I was as a person, I have been living in a constant existential crisis. Another trigger for me was the end of my hockey career, which I had dedicated fifteen years of my life to. We won this final game, and everyone else was skating around the ice, so happy. But I just went completely numb. Like I was like, holy crap. Fifteen years. This was supposed to be the moment. And I felt nothing. 

Something that came in here was actually my first psychedelic experiences. A lack of knowledge about how powerful those substances were, how to integrate a lot of these things that we now know because of the recent research. And there was such stigma around it that there was no one to connect with and talk through it. Then, seven days after my 21st birthday, my dad had a heart attack. He lived, but all of a sudden this trauma from childhood was triggered as I was going through these psychedelic experiences. All of this accumulated at once, and I ended up as an inpatient in the hospital. This was the most difficult time in my life. Canada gets a lot of love for its healthcare system, but there’s still a lot of shortcomings specifically around mental health. It made me realize that the onus is on us to self heal, to understand ourselves better.

For lack of a better term, I felt crazy because everything was in my head, and it became this process of how can I get these thoughts out as quickly as possible. For me, it was Evernote at the time, and then a lot of audio and video recordings, just talking and processing through things. And I saw a strange gap. First of all, why was there no system that holistically combined audio, video, and text? These are some of the most popular mediums to express ourselves. Why did the system not give me any insights back into myself? That’s what began the journey of what we’re building and working on today. Of course there’s a technology, there’s a platform, but it’s not about that. It’s about the methodology, it’s about the self analysis and understanding yourself better. It’s about the hope that we can build a community where we all lift each other up and help each other too. 

Thanks so much for sharing your journey. It’s amazing when founders have a deeply personal motivation for building a product. Talking about the community, what kind of people use Speak Ai today?

Oh, it’s very interesting. We’re still early, but we’ve tapped into a root part, which is communication. There is communication with others, which is what we traditionally think about with communication, and there’s  communication with ourselves, the self-talk that’s going through our head. It can be very positive and uplifting, or completely negative and debilitating. So we have a very wide range of people. For example, qualitative researchers who are going through an interview with someone and trying to understand their needs, desires, and pains. We also have self quantifiers, who just want to dump all of these thoughts and then get a measurement back.

One of the exciting things that we’re really pumped about is the ability to import files with their original metadata, such as creation date and time, longitude and latitude. So you can connect the notes to the location, the weather at the time, all of these amazing meta details. By retaining the metadata, you can automatically surface these insights that you had never seen before. Because of that flexibility, we have people using it for different reasons.

Amazing. What’s a particularly surprising or unique use case that you didn’t expect?

I’ll give you two. One of them was a simulation center at a hospital and they were reenacting crisis situations where they would bring residents or doctors in, and what they were looking for was communication breakdowns between the residents and the doctors that could have detrimental patient outcomes in that situation. Another one was a residential inspector. They recorded all their inspections through audio and video then automatically surfaced this information and printed it into a summary. So, at the core level, we’re helping people find the information that matters, even if that information is wildly different from party to party.

Can people on the platform learn from each other’s data or patterns? Is there some form of collective intelligence developing by using such a platform?

I would absolutely love to do that. Right now, we’ve built the first part. For example, you’re a writer, you’re constantly taking notes and writing. We’re trying to help you find and connect the patterns between all the notes that you’ve ever written. It’s not just texts, we can find connections with audio and video too. So that’s been the first initial part. The second part that you’ve touched on is really powerful. Sometimes it’s really hard to understand who we are when we don’t know who other people are. If there’s something that can aggregate those to create a comparison model or just a baseline measurement for you to help understand yourself, I think that would be beautiful. We’re in the very early stages, but it would be an amazing way to inspire and inform each other.

That sounds amazing indeed.

The part that’s really interesting is that you could start to learn about yourself in real time. You could understand yourself to help you course correct. If there are indicators that you’ve identified that are showing that you’re on a downward spiral, you could get that notification in real time before you have to go down that path, so we could help people avoid suffering. And then on the more positive side, if you’re actually trending in the right direction, we could help reinforce that so you can continue to grow. That’s the part that is really deeply inspiring to me. If we can stop people from suffering or just help people grow… What a life to live! I’d be very happy about that.

This is such a great mission. I think so many people could benefit from more self-reflection, but all the tracking and analysis may feel a bit overwhelming. What do you think?

I think there are two channels here. One of them is based on manual input, which can quickly become frustrating. The second is through unstructured written or audio notes. You’re actually creating connections that become very valuable for you without too much work or overwhelm. So how can you capture these connections in a more seamless way? For example, “I feel sad when it’s cold outside” or “I feel happy when I talk to Anne-Laure.” Now through relatively unstructured writing or speaking, you’ve actually started to quantify. And I think that ability is going to really bring down the barrier for a lot of people who feel overwhelmed by the process. 

Thank you so much, Tyler! Want to follow Tyler Bryden’s journey? Follow him on Twitter or sign up on Speak Ai.

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