Strategy Sprints · 2026-06-23 · 29 min
Key moments - from our scoring
Substance score
37 / 100
Five dimensions, 20 points each
Simon Severino and Monica Bozinov discuss practical AI implementation for reducing cognitive load - not the hype, but real productivity systems they've built and tested. Simon details his multi-role GTD setup (husband, father, CEO, athlete) supported by Claude, which connects to his health coach's Google Doc, Whoop band biometrics, and sleep tracking to deliver contextual reminders (like adjusting breakfast before evening workouts). Monica shares how Claude remembers her preferences, keeps her focused despite distraction tendencies, and gamifies task prioritization - telling her to stop working 15 minutes before meetings instead of pushing through. Both emphasize that AI only works when connected to your actual context: emails, calendars, Google Docs, Slack, meeting transcripts via tools like Granola or Obsidian. They use Claude and Claude Code rather than ChatGPT because Claude remembers proprietary data and learns your preferences over time. The episode walks through three AI 'advisors' - health, spiritual (using Marcus Aurelius stoicism), and behavioral - that provide feedback on gaps between stated goals and actual actions. Founders drowning in context switching will find concrete setup examples (10-minute health doc, simple strength/mobility tracking) and a monthly workshop roadmap (April through December) for building a 'board of advisors' across sales, marketing, content, revenue intelligence, and delegation.
Connect Claude to your Gmail, calendar, Google Docs, Slack, and meeting transcripts (via tools like Granola or Obsidian) so it knows your actual context - your health routines, preferences, relationships, and goals. This takes about 10 minutes to set up and allows Claude to remember who you are and provide contextual help instead of generic responses. Start with Claude Code rather than ChatGPT, which operates as single Q&A instead of holding ongoing context.
Simon uses David Allen's Getting Things Done approach, organizing life by roles and responsibilities in order of importance: husband first, then father, CEO, and athlete. He uses Claude to help manage context switching between these roles and prevent the CEO role (which pays rent) from consuming all attention and energy, ensuring he stays balanced across all commitments.
Simon created a simple Google Doc listing his weekly activities (Monday mobility, Tuesday strength, Wednesday mobility, Sunday rowing), wears a Whoop band to track heart rate variability and sleep quality, and feeds this into Claude. Claude then gives contextual reminders like 'less honey in your coffee' before evening workouts when cholesterol will spike, and tracks sleep scores (he achieved 99% recently versus his normal 81-86% baseline).
Move everything from ChatGPT single-question chats to Claude and Claude Code, then connect Claude to your actual data sources (Gmail, calendar, Google Docs, Slack, transcripts) so it understands your context, preferences, and patterns. Without this connection, you'll only get generic 'slop' instead of personalized help.
Simon uses a 'stoic' AI advisor (modeled on Marcus Aurelius) that monitors whether he kept his cool or let emotions derail his behavior. It calls out patterns - like anger or fear that undermine his values - providing feedback quickly (via Discord messages) rather than requiring weeks of reflection, building self-awareness about what triggers him.
Our reviewer’s read on each dimension, with quotes from the episode.
There are a few genuinely useful distinctions - chatting vs. agentic AI with persistent memory, connecting Claude to proprietary data sources - but the episode is dominated by personal anecdotes, motivational framing, and meandering conversation. The ratio of novel claims to filler is low for a 29-minute runtime.
You will get slop until you, you connect it to your actual context.
stop doing chat. Chat is a single question and answer game. That's not what we were talking about. We're talking about your proprietary data.
The core arguments - connect AI to your calendar and email, give it context about yourself, use it like a coach - are widely circulating in AI productivity discourse. The 'board of AI advisors' framing has some novelty, but it is underdeveloped and quickly pivots to a product pitch rather than first-principles reasoning.
I have told my, you know, my main agent, like these are my weak spots, right. I, I get distracted easily.
it looks at what I say and what I do and what's the gap?
Simon Severino is a genuine practitioner running a consulting firm and advising 253 companies; Monica Bozinov is a collaborator rather than a traditional guest. Both are real operators but at modest scale, and the format is a co-host chat rather than an interview with an independent external expert.
advising 253 companies in the sprint club
Running a consulting firm, executing monthly coaching in public, recording an audiobook, hosting the sales show, being on the rowing team
The episode is above average in named specifics - exact tools (Claude Code, Granola, Obsidian, Whoop band), concrete sleep score data (99% vs. 83-86% baseline), a 10-minute setup claim, and a rough cost figure - but all evidence is purely personal anecdote with no external benchmarks, case studies, or business metrics that would transfer to a listener's context.
it's in the 80s, so it's usually 83%, 86%, 81%, 79%. That's my normal sleep score. And then I wake up here with a 99% sleep score
It took me 10 minutes to set this up
This is a friendly co-host conversation with minimal challenge or probing; questions are generic prompts ('what do they do?', 'what was your sleep score before?') and the hosts consistently validate each other. The episode ends in an explicit product pitch for Jetpack workshops, undermining its educational credibility.
If someone is watching now and they don't know where to start, what do they do?
I see a health coach in my future.
Computed from the transcript - who did the talking, and the words that came up most.
Join 250+ B2B founders in Sprint Club (free 7-day trial): In this episode, Simon Severino and Monica Bozinov share how AI tools are reducing cognitive load, cutting context-switching, and giving them back hours every week.. without the hype, without the technical overwhelm.
Transcribed and scored by The B2B Podcast Index.
Simon Severino: Welcome back everyone. Monica Bozinov and Simon Severino. Today about how AI can save your life, how it can be a, ah, life hack. Something that makes your life better immediately now you might say, oh, that's the hype. All these skills, all this stuff, it's not technical at all. We're going to share from our own life and how we are chronically overwhelmed usually, but much less right now with all these helpers and how they actually help and how you can set it up so that you have a better life right now, this week, this month. Welcome, Monica.
Monica Bozinov: Good morning. Buongiorno, M. Simon. Ah, yes. This is, um, finally one of those episodes where you and I get to talk about how it changes our lives. It's not about the hype, it's not about the next skill. It's not about, you have to learn all the technicalities of AI. Just start somewhere, uh, with the things that are, that will be the most beneficial for you. You and I do not have the same system in place, but we're both testing like, we're both like jumping into the water and testing what we can do with it. And I think that's where you need to start. You can read all of these articles, right, uh, that will, that are really scary and feel super behind. Even though even if you're just testing AI right now, you're actually ahead of most people.
Simon Severino: Let me share a post that I shared, um, yesterday, I think on um, on Facebook. So I said I got to bed every night absolutely freaking exhausted. And I love it. Running a consulting firm, executing monthly coaching in public, recording an audiobook, hosting the sales show, being on the rowing team, advising 253 companies in the sprint club, co parenting three young humans, managing three investment portfolios. Most people would drown in the context switching. I don't. Not because I'm built different, because I built a system different. Claude runs underneath all of it. Account dashboards, updating in real time, forecasting audits. I used to dread meeting agendas drafted before I even open my laptop. Email triage that protects my deep work. Weekly prioritization that actually reflects what moves the needle. Five simple workflows. And that's the difference, right, between, uh, the business runs me or actually the business supports my life. Right? And I didn't even add that we were creating hundreds of vacations over the last weeks with the book launch. So lots going on, right? Like everybody listening. Lots going on in life and in business and just the context switching. So right now it's 9am in the morning. I was recording three chapters of the audiobook, which I've never did, never done so, so much to learn, so many moving parts. And then I was booking a romantic weekend, uh, for my wife and I in a few weeks. And the, the book, the hotel canceled on us. It's a small boutique hotel and so they canceled on us. And I had to find something new. That context which I'm recording, I have to switch context usually would have taken another hour of work. Now I just opened the terminal on the side I was still speaking the audio thing, but on the side I was saying, hey, we need a new room. Uh, but it needs to be in, in vineyards like this one and it needs this kind of stuff. Uh, and it was generating three more options and starting sending emails to this hotel and seeing if they have availabilities. So something that would have kind of destroyed my morning because I can't be totally here and totally there is much easier to handle.
Monica Bozinov: I saw this really funny reel on social media. Some stand up comedy comedian who said, whatever problem you have when um, life is really hard and you're going like, ah, uh, it's so difficult right now. She said, add a baby. I mean, not really, but in your head.
Simon Severino: Add a baby or three.
Monica Bozinov: Yeah. And now take away the baby that's in your head and the problem isn't that big anymore. Right?
Simon Severino: Exactly.
Monica Bozinov: It's just another day. And that is kind of what AI is doing for me right now. It's kind of taking away the baby in my head because I don't have to switch all the time. I don't have to find the next system. I can stay in one lane and I can say, oh, by the way, this just happened. I don't like that. Can you fix it? And it fixes it with, without having me, without me having to jump around. And I think that is one of the biggest wins. And I have told my, you know, my main agent, like these are my weak spots, right. I, I get distracted easily. I run for the next shiny object really easily. Right. Uh, I get lost. I'm um, kind of time blind. And now it knows and there are more things I need to put into it as I start working with it. But it keeps me on track and I can even like physically leave and they come back and I can continue in the same space on the screen so there's no cognitive load like, oh, I have to open the next thing. And it's like, ah, uh, it's like what someone said. It's like a warm cup of tea right?
Simon Severino: Yes, guys, that's the difference. Right? And you will hear many. Yeah, but I don't experience that. And when you dig deeper, and I hear that 10 times a week, um, mine hallucinates. Mine doesn't know who I am. Mine doesn't know what kind of hotel room I want for my weekend with my wife. And then I, I say, okay, share screen, show me what you're using. First thing is they are usually not using Claude, they're using ChatGPT and it's not the product that's such a difference. The difference is that Claude remembers who you are and works with your own proprietary data. So how you like to book a room, how you like to run things, and that makes the difference. It's not which model is, um, more capable right now. That changes every week. The models are all good enough right now. They are all at 70%, 80% of what we need them to do, which is good enough for this kind of things, that we just, uh, share it. The point is it will only start working for you when you connect it to the context, to your emails, through your calendar, to your actual weekend. What are you going to do on the weekend? Um, to your, for example, my, my health coach. Right. Or my spiritual coach. They're so helpful. Health coach gets my, my blood work and knows when I train. So today's Thursday. Tonight I will have a hard workout with the rowing team. It knows that my cholesterol will spike. And it, it reminds me, hey, less honey in your coffee, more, uh, oat bran. It's one of these. It's not oats, but it's one of these, uh, variation of, of oats or a different part of the plant that has more, more things that buffer cholesterol, basically. So I change slightly my breakfast because I'm reacting to what's needed of me in the evening.
Monica Bozinov: Yeah. So the more context, like, you have to raise it, you have to teach it, and you have to make sure it has the right memory. But then it knows you and then it will give you those, it will give you that support. Yeah, Yeah. I, I found, I found out, like last night I was it. I said, okay, Now I have 30 minutes and we have all of these tasks. And like in 30 minutes I have a meeting. So what would be, like, what would be a good thing to do right now? And it started like, we could do like one of these three things because I'm like kind of putting my brain into it. Right? And oh, yes, let's do this. That was like, we can do that. And I just said, yes, let's go. And um, and it kind of just did the thing and I can relax while it's doing the thing. And then it did the next thing and I was, I told it. I kind of like this when you said, okay, now we have 15 minutes left. Right. And it kind of gamified it for me.
Simon Severino: Yeah.
Monica Bozinov: And then it said, so what can we do now? And it said, well, uh, let's stop for now. And you go to the meeting. Present the meeting that starts in 15 minutes. You be present for the meeting. And I would not have given me that much slack. Right, right. And I was like, oh, that's a brilliant idea. And it was such a, like, uh, a uh, gift. Right. I have programmed it like I need this. But then when I experience it, it's like, oh, it gets me. I told it what to do, but it gets me. Right.
Simon Severino: And you forget it in the moment because you're a human being. But, but it's a machine, so it remembers.
Monica Bozinov: Yeah. So I was like, okay, let's chill. I can just, you know, wait, I have 15 minutes and I'm not. And then I went. And then it said, and after the meeting you can come back. And I was like, no, I'm not coming back.
Simon Severino: Mhm.
Monica Bozinov: Because it's late for me now. It's like my day is over, but I will be back in the morning. So like I make the calls. But it's so nice to have some. Something.
Simon Severino: Yeah.
Monica Bozinov: Because it's not someone, but something that reminds me of the things that I tend to forget about me.
Simon Severino: Yeah. My own limitations and listeners might go right now. Oh yeah. But uh, it's too much effort to train it. I cannot spend so much time training it. Let me show you all the information that the health coach has. Okay. It took me 10 minutes to set this up. Uh, and of course it will get more context over time. But the setup is 10 minutes. This is everything that Ben the health coach has. It's a Google Doc. It's called Health and it says Monday mobility, Tuesday strength, Wednesday mobility, Sunday rowing technique and some weightlifting. So it's a few sentences. If you are listening to this and not watching it. It's a simple Google DOP gog doc with one sentence per day on basically what Simon's weak in in terms of health relevant activities. Ah. Which is basically, uh, what am I doing in terms of movement? And then that's it. And then there is learnings. Mhm. So this week it learned that my sleep score is 99%. If I do my normal workout during the day, but in the evening I took two specific things that it told me to take. And I never in my life thought about sleep quality. I was more like Ozzy Osbourne, you know, rock and roll and whatever. Take me off stage whenever you want to. Right. Uh, I don't care. It's rock and roll time.
Monica Bozinov: But what was, what was your sleep score before this?
Simon Severino: Nobody knows. Uh, well, it was always unmeasured, 46 years long. But then I started and it's in the 80s, so it's usually 83%, 86%, 81%, 79%. That's my normal sleep score. And then I wake up here with a 99% sleep score, which means totally refreshed. And I felt it. Right. Uh, it was really good. And it says, just do these two things and it's good for you. This is, this is a very important learning. And what did I set up? Just this simple Google Doc. And there is no complicated Huberman style 700 metrics or. It's very simple, it's very simple. The days alternate with strength or mobility and some days it's technique. That's it. And there is a whoop band on my bicep that, that measures heart rate variability and how my body responds to training in terms of stress and recovery. And the third metric is that sleep quality in percentage if I slept well or not.
Monica Bozinov: I, I see, I see a health coach in my future.
Simon Severino: Um, right. And. And it costs 200 bucks a month instead. No, it costs a bit more because the woo band is expensive. But Claude is not. And not blood work is not in Europe. So.
Monica Bozinov: Yeah, yeah, yeah. I, I actually like this week. So it's both Tuesday and Wednesday. I left the office feeling like I'm on top of things instead of so much I need to remember so much I need to keep in my head or get down on paper because now as I'm putting all of this stuff into the system, it remembers it for me. And I can find everything in one place. All of my projects, all of my tasks, um, everything I need, you know, still need to put into it, building like a knowledge base. And it's, it's really soothing to my brain.
Simon Severino: Yes. The other two helpers, one is spiritual, one is more behavioral, but both very simple. They look at what I say and what I do and what's the gap? Right?
Monica Bozinov: Yeah.
Simon Severino: And so one looks at the strategy page versus the, the dashboard and says, hey, you guys say that this is your main goal, but you are doing this. Which doesn't contribute. M. Super helpful. The other one is, uh, after Marcus Aurelius, it says if I kept my cool or if I let the world go under my skin and then actually derail my best possible behavior instead. Coming from anger, from fear, from, you know, I lost my stoic posture. He wants me to be stoic, which I rarely am. But the important thing is this feedback shows me where I derailed. Right?
Monica Bozinov: Yeah. So it can actually help you get a higher level of self awareness because it will, it will call you out.
Simon Severino: Yes. And you learn about your patterns. Right. What can get under your skin so that when it happens again, you go, oh, oh, this is an invitation. Right. This is a trigger. Looking at me. I can decide now.
Monica Bozinov: Yeah.
Simon Severino: Uh, I'm not a victim anymore of this situation. So there was a guy, he came onto the show, and then in the 10 minutes after the show, I met him only twice. M. And in the 10 minutes after the show, he asked me for an introduction to a very important person that I know. And I met him only twice. So I said no, because, you know, it took me 10 years to build that relationship and it was opened to me by somebody else. So I would have to ask this other person because it took them a decade to build that relationship and to open the door for me. And so I forgot it because I had two more minutes to go into the next ZOOM meeting. So I forgot about it, moved on. But then on a Sunday, I get, uh, Romano, my spiritual coach, uh, mentor, giving me feedback, says, simon, you handled that boundary well. That is our virtue. Integrity. You, you protected a relationship that took decades to build from an opportunistic situation. So, uh, and validated that it was the right thing to do. And why and how this in the context of relationship integrity. So why it matters, Right? Because a business, in the end, is building relationships and keeping them protected and nurtured. Uh, that is what business is.
Monica Bozinov: Mhm. Yeah. And that's very different. Right. Because I see people using AI, they tell me that I have a coach, I have an AI coach. And they're using it for, um, to get confirmation and support. What you do want is to have it be your guardrail and call you up on the weaknesses that you, you know, you have. Because it's, it's kind of programmed to, to uh, you know, be compliant and to build you up. So you have to give it instructions like, this is where I need help. And that takes some self awareness. But what I like about it is that, uh, it's easy, like it's Easy to take that feedback and run with it because it's like, oh, yes, of course I asked it to do that, But. But it does help you create some guardrails around your own behavior.
Simon Severino: Totally. And, you know, I'm not upset listening to this and saying, oh, yeah, you're right. You're actually. Yeah, you're right. Okay. How can we improve this? What can I do better? Next time you get that feedback, you move on.
Monica Bozinov: Yeah.
Simon Severino: And it doesn't take me two weeks of a meditation retreat to get there, but it's. It's a quick discord message that I'm getting in between.
Monica Bozinov: Yeah, yeah. And when we've. When we do have a level of self awareness, then this is really helpful.
Simon Severino: Yeah. And the context switching is real. So I use this GTD method, getting things done that I learned from David Allen, where you have different roles and responsibilities in your life. Right. So. And I rank them by importance. The most important is husband, because, you know, the kids at some point will grow and go away, but there is an order in the system. Right. Um, who made those kids? So there is a partnership. The. The marriage couple is more important. And so it's. The first role is husband, and it has some roles and responsibilities. Right. Somebody married me, so they, they were expecting something. Right. What are the expectations? How will I show up? How I, uh, will I become better at it? Right. Over time, rather than slowly degrade, like you buy a great car, and then after 10 years, it's like, oh, this car stinks. Like, how can you stay? You know what, what the promise was in the beginning, over decades. So that's a project husband. Then there is. And today I was working on this romantic weekend, um, next project. Right. Uh, father of three, CEO of a business athlete. Because I have a body if I want it or not. And so you can use it or lose it. It's simple in the end, I mean, it will, um, decompose anyways. But right now you have it. And so it can be your vehicle or it can be a blocker.
Monica Bozinov: Yeah.
Simon Severino: Because you want to write a book, but you are feeling your. Your neck all the time. Uh, so if you want to show up in, in all of these roles, you need energy. And that energy comes from the body or can be blocked by the body. Right. And so when I go through them, that's actually a huge context switch. M. And it was hard for me to actually be good at all these things. Usually I picked the most urgent ones. It's usually CEO. And then, because that pays the rent. Right. And so. And then CEO gets all this attention and all the other roles start having less, less, Less attention. Budget. Anything Budget. And I'm.
Monica Bozinov: Yeah, yeah. Because we are limited. We are limited and we need to put the focus where it serves us the best. And we're not always really good at that. So it's really helpful to have something that keeps us on the. On the straight and narrow. Where we have said that we wanted to move. Right. Uh, so um, if someone is watching now and they don't know where to start, what do they do? Simon, they want. They want to simplify their life. What do they do?
Simon Severino: I would start moving everything to cloud code away from your chats because stop doing chat. Chat is a single question and answer game. That's not what we were talking about. We're talking about your proprietary data. How you eat, sleep, do move, behave and having that in a loop that creates improvement and learning all the time. So you're turning into a self improving system and a self healing system and a self correcting system. A system that compounds knowledge. Over time you learn about yourself, your clients, the people that matter. And you get better and better at what you do all the time. In order to do that, you have to select one LLM that can actually do that. So for us it's Claude. And we moved away from chat because we use only Claude code. Mhm. Some things can be done by Claude code work too. But Claude code is the actual helper. That's the thing that can actually do work for you.
Monica Bozinov: Yeah.
Simon Severino: And it remembers.
Monica Bozinov: Yeah. And if you only have tried chatting with GPT or with ChatGPT, I mean that can be helpful. But that's not what we're talking about here.
Simon Severino: No.
Monica Bozinov: And you haven't really tried the system until you move on to the next step.
Simon Severino: Yeah. You will get slop until you, you connect it to your actual context. And in cloud it's using the connectors. It's cloud settings. Ah, connectors. Connect to your Gmail calendar, Google Docs, wherever your life is. Right. Connect it to your. To your slack group, whatever. Wherever your life happens. Uh, your meetings transcripts. For us it's granola Obsidian. Now it knows who you are. And now it can actually help you. Now it can say. It can say, hey Monica, I know that now it's this time. Now you like to wind off. So I will summarize everything document. I will take it from here. See you tomorrow.
Monica Bozinov: Go and get 99 sleep.
Simon Severino: Exactly, exactly. And it reminds you. Right. So yeah. Uh, before maybe you drink a chamomile tea before, before you go to bed. Now it can actually help you.
Monica Bozinov: Okay, this is, uh, so the AI now is a lifesaver for you. I certainly feel it's making my, like, my cognitive load way easier. I'm calmer when I leave the office. And I am, uh, more, um, happy to get started in the morning. And I'm like, three days into using it more properly.
Simon Severino: Sounds powerful. And we have a monthly workshop if people want to build this with us. We started in April with the foundations. Now the major workshop will be building your board of advisors. Like your, if you want to build your health advisor, wealth advisor, whatever, right? Your sales advisor, marketing advisor, you can do that in the May session. In June, we're going to build the sales pipeline processes in July, the content machines, all the marketing in August, how you onboard clients, make them happy, activate their success, visualize their success. In September, revenue intelligence, October, delegation, November, creating, uh, even more loops that learn week by week. And then in December, you should be only doing the five tasks that you love doing and are great at. And then everything else should be handled for you. That's the plan in the Jetpack workshops. People can find them@strategy sprints.com and I
Monica Bozinov: have already, um, started thinking. I found, I saw this woman, uh, on a podcast. I was like, I want her on my board.
Simon Severino: Let's do it. Main Jetpack workshop. She will be on your board. Let's do it, guys. Let's build Monica's board in the May session. See you in the May Jetpack workshop. Whoever you go, I want them on my board. Write it down, bring it to the Jetpack workshop. We're going to make it happen.
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