April 8, 2026
I am always perfecting my daily routine, I find this enjoyable and makes me feel like I am becoming a better person. So here are some new things I am doing.
I recently got an Apple Watch, and I have been loving it. I got one about 8 years ago but thought it was making me too attached to my phone. Now, I can't afford to miss any texts or emails since I have a responsibility to my customers.
I have been enjoying the workout feature and tracking my heart rate. Turns out my resting heart rate is pretty low, I am assuming because I workout a lot.
I love the mindfulness app on the Apple Watch, I meditate once a day for 10 minutes already, but I do "mini-mediations" a few times a day using it. I also log how I am feeling in the app, and use the reflect functionality as well.
One of the most challenging parts of my day is the morning shower for me. I have a lot of negative thoughts during this period, normally I journal to remove them but it's difficult to do that in the shower. So, I got a shower journal. While I shower, if I have a negative thought, I categorize it by tallying them in the shower. I think it gives me more control and I have been liking it so far.
I haven't drank in a while still. When I go out I normally get a non-alcoholic beer. Now, I am going to get soda. I don't need the carbs.
I used to wake up early and go on a run on Mondays. While rewarding, I stopped doing it. I think it's better to have a regular routine for my body. It didn't like waking up at 5am.
I joined a kickball IM, so I allocate 4 hours on my Sunday just for socialization. As an extrovert that is cosplaying as an introvert, this is important for me.
The day before, I schedule what I need to do for the following day. This is helpful for me to know what I need to do, but I want to ensure I am mostly selling and doing some building. Color coding my calendar makes sure I am aware I am doing the right things.
I used to do discovery calls, take notes, and likely lose the notes afterwards. Now, I use air table to take notes and write key details of all my discovery calls. This is important to keep track and know what I need to do next.
At the start of the day, instead of just getting to work, I review my schedule and make sure I understand what my priorities are.
I write letters to everyone that meets with me. This has been quite helpful for me to keep in touch.
I kept on missing my friends birthday's and it really upset me. A couple years ago, I put them all on my calendar. I still used to miss them, now I schedule send all my birthday texts, now I never miss any birthdays.
Best,
Ben
April 5, 2026
After my pivot I have definitely had some analysis paralysis. I didn't realize that until I spoke with a fellow entrepreneur and they mentioned that. This analysis paralysis is also made worse by my shiny object syndrome.. I think the reason I have these traits is due to my fear of rejection and not having a cofounder to help keep me in check.
Typically my pattern is that when I hit a friction point I tend to fall for this shiny object syndrome. The most likely reason is my brain looking for a way out.
Finding clarity in this "analysis paralysis" is aided by separating the signal from the noise. Which I'd like to become better at. Building a startup, so far I am not so sure I am too good at separating the signal from the noise. I am much more of an "action produces insight - Brian Armstrong" kinda guy. I also think I am making a mistake by listening to too much startup podcasts and entrepreneur content. Most advice is pretty dumb and I think I listen to a vast majority of it.
One thing that really helped me was to have a set of frameworks that help me structure the way I think about my startup product strategy. I listed some of them on the frameworks section and will add more as I encounter them.
So what am I also going to do to stay more focused and separate the signal from the noise?
I'm going to listen to less entrepreneur content.
I am going to talk to customers more.
I have blocked twitter for the next week on my computer, that helps as well.
Build out more frameworks.
In health,
Ben
March 22, 2026
Our entire lives are shaped by the people and the environment around us. You are probably thinking, this guy is just saying the obvious thing. Which, I am.
I also think I am actively getting shaped by everything around me right now. Here is a list:
What first comes to mind:
Reddit, the thing I want to reduce the most of. The only social media I can't kick. I used to love Reddit back in high school, now it's just holding me back. The comments and posts are people that I know I wouldn't want to hang around in person. I just don't know what to look up when I am on my phone or on the toilet.
In person, mostly family and friends. With how my career is going, I sometimes feel like an outlier. Id prefer to find other circles, just hard where I am physically.
Books. I read a lot of business and self help books which are good, but what I need to remember is everyone's path is different and their advice and opinions are not one size fits all.
Podcasts. I think this is one I put sometimes too much weight in. I listen to tons and tons of podcasts. But, just because someone has my ear and attention does not meant that they deserve it or that their opinion matters/ is correct.
Twitter. A place I am trying to figure out how to manager. I feel like it has good information, but man it really sucks sometimes.
I am saying all of this because I love Sunday evening for preparing for my week. That is what my Sunday normally is, journaling, writing to-do lists for the week, accountability forms, updating my google calendar for what needs to be done.
I figured out that the way to start all of that is to reduce my inputs. Everyone online or in person that is fighting for real estate in my brain needs to be calmed as I prepare for the week. This is superrr important because I mostly judge the outcome for my week based off of my performance that is dictated by what I write down for my goals or my to do lists on Sunday evening.
Finally, I do this by meditating in the video I have linked in my "routine". That is how I clear my inputs.
March 20, 2026
Building a business is hard. I face constant rejection. As a tangent, my rejection is more "we will evaluate this in a couple quarters," or "send us an email." Being told no is actually quite rare. It's more of a soft rejection. However, going and introducing myself cold in offices, or calling offices, or going up to others at conferences is hard. I have gotten to a stage where it feels normal, but it's still hard and it definitely still gives me anxiety.
What helps me is I ask myself why I do this. Initially, I wanted to start a business because I remember looking out of my cubicle wondering what I was doing there, knowing that a startup was my eventual path.
Knowing that you want to do something and actually doing something isn't easy. There's a vast chasm there that some people never take the leap of faith in.
A word that best describes this leap of faith is courage. I never really thought of the word courage. But courage is what it takes.
Finding courage is hard. To have courage is to have strength. I found my strength in figuring out my why.
Once you have purpose, you can have strength. Earlier I spoke about the Mormon. His purpose was God, and that allowed him to have the strength and therefore the courage to get rejected every day and convert one person a month. We are talking about out of the 300 people he spoke to a month, he converted one person. That's some fucking courage.
My why is building schools in Asia. Thinking about the kids I met that I can help, that every day that it takes me to build this business is one day less that I could've helped them.
That's why I am doing this, and that's why I won't stop.
March 20, 2026
In my previous product, on a good day I could hit 5 offices. Now I am selling an AI-enabled service that I can eventually productize. Yesterday, I went to 12 offices. It took me roughly 2 hours. On Monday I will go to 20.
I know that what really matters is sales, so if in my previous product I could sell to all 5 offices. It would still work out. But, I couldn't so I would rather have a larger pool to fish in.
Going and selling was a (inserting startup buzz term here) forcing function to actually figure out what people wanted.
Now I am selling a service that is directly related to a problem that everyone is trying to solve in the field.
The funny thing is, I don't have a product. I am going to these offices and selling a flyer.
I have incredible founder market fit in this area because I solved this problem in our office through spreadsheets and code but I wouldn't call it a full product.
Not having a full product is a good thing.
What I learned from my last venture was I tried to build the full product then sell it. Yes, I was trying to ship fast but still I am a solo founder.
So now, I am selling something I haven't fully built. I get to spend every day focusing on figuring out what people want.
I will be able to know this because they will tell me what they want and I am going to build it next.
I am superrrr into mantras now. The one I like the most right now is "Show me your calendar and I'll show you your priorities" I am in the stage of customer discovery/selling/making something people want. So, my calendar is mostly sales calls, time for cold outreach (email/in-person/phone), reaching out to my network.
I havent coded anything in a week now (I do have a claude agent scraping leads at the moment) but that doesnt count.
My goal by next week is to pre-sell to 5 people. I have 1 in the pipeline, now I need to find four more.
March 16, 2026
Months of fumbling around talking to customers might not mean that I have much revenue to show for it. But, I have been hanging around the rim. That allows me to stay in the game of this startup journey. That's all I ask for. One thing a founder should not be doing is staying in their room. Going outside and talking to customers is so crucial, nothing else matters. You never know what that next meeting, conversation or referral might do for you. I know that what I am building now has real value. That's because it's already working in my office. I know that other people want it because it's solving a top 2 problem in the dental field. I aim to pre-sell this week. That means getting on calls with business owners and having them sign off to my business, then build the fully fledged product after.
This is what shows the clearest signs for PMF in early stage. I spent 3 months building a product then selling it. Turns out after building a product for 3 months, no one wants it. It wasn't a waste of 3 months by all means but it could have been more efficient.
I'm okay with that. I don't like to just call what I am doing a startup but more of a journey. That is what building a business is like, embarking on a mission where the destination is not clear, just making sure to put one step in front of the other.
March 10, 2026
Today I had three sales calls. Just getting three sales calls should be something I should celebrate.
I think im really bad at sales. Especially on Zoom. I am going to need to write down a list of customer objections just so I can answer them. I also am going to order a couple books.
My fears about my product are coming true. Turns out it doesn't solve a real problem that the customers need. I am absolutely certain that I am going to change my idea.
I am saying change my idea because I am going to reserve the word pivot for a company with > 10 employees and real money put into their product. I am just a dude that lives at his parents house trying to build products people would pay for. So, I am going to say I am changing my idea.
Changing your idea should feel light, and my next idea is something that I really think customers want. Why? Because whenever I pitched them my current product they asked me to work on this instead hahah. I just wasn't listening.
Still, I am not going to code. I am going to make it my objective to "pre-sell". I need 5 people at least to say they will buy this when it's built.
The next thing will be hard, that is without a doubt.
But, at least my challenges will be more technical than market. Technical challenges can be solved. Market challenges cannot.
Best,
Ben
March 10, 2026
How do you get users?
How do you make something grow?
Are you making something people want?
March 8, 2026
Evaluating a startup is emotionally taxing. I have worked on a product for months, and am trying to sell it now. There is a lot of emotion involved.
Emotion won't get you customers, or Product Market Fit. I have to be tactical with my decisions.
I want to be as objective as possible, so I wanted to use one of the most objective techniques I have ever used. The scientific method.
Building a business is an extension of the scientific method. Usually, someone has an idea and they want to test it in the market. Structuring my startup like this makes my decision making process more objective than looking back at December, January and February as months of me building a product and now I am trying to sell it.
That brings emotion into the equation.
My scientific method went generally like this:
I believe that X customer that has Y problem would pay Z amount.
Can you speak to X users and would they pay? If it's hard to find these users what does that mean?
Can you make a living salary off of this business?
Come up with conclusions and make your decision.
March 7, 2026
After my time trying to start a company, and my trials and tribulations. I think I figured something out. Once again, I think. Starting a company is like those solicitors on a busy sidewalk with a petition in hand. Now that I moonlight as a solicitor sometime, I tend to cut them some slack.
As an early-stage founder, you are the solicitor. You should be the person with a petition in their hand. You are petitioning your future self to work on a project. Building a company, time is your most valuable asset because everyone has a timeline or a deadline for how long they'll be working on their business. You should make sure that when you are building out your company, you are spending your time on high-leverage activities.
This is incredibly important. I was listening to a podcast and in the podcast they're saying that before the startup, the build phase, there's a research phase. If you don't do the research phase well enough, you're going to be doing it anyways after you build the product, when you try to sell to customers.
I see what he's saying now because I'm in the research phase. Turns out that if you don't do enough research beforehand when pre-build, you will figure out whether or not this would be a real business after spending months building out the product
This petition is an analogy for talking to customers. You are going to need to talk to customers and to ask them, "Is this a problem you have?" If so, will you sign this petition or will you sign this future work order to buy this product?
After going into over 10 offices this past week, I found that this is the best way because you can directly go to your customer with mock-ups of the product and if they tell you that they will buy this next week and you make up some kind of reason that it actually can't be done next week, then you build a product.
I know this sounds antithetical to a startup where you want to build an MVP and ship it fast but at least this gives a lot more clarity on what to work on.
Ben
March 5, 2026
The more difficult conversations you have the better your life will be.
There are two types of difficult conversations you can have, ones with yourself and ones with others. Joining the workforce after college allows you to have few difficult conversations, save for a salary negotiation or maybe an interview. That's comfortable, and fine for others. I am at a point where comfort is not what I am seeking, growth does not lie in comfort. It is on another plane. This week I have knocked on 10 doors of offices to show them my product and had one sales meeting.
The hardest question I have asked someone this year is if they would pay $x amount for my product, but I did it. Their answer is pivotal to my journey of starting a business. It has taken me a lot of time to understand that the answers to my company aren't going to be found at home. I tried to find them by solving problems while working in the family office. But, the best method is to talk to as many people you can.
Your customers will tell you their biggest problems. They will beg for you to make the solution and are waiting for you to say you have solved their problem in a certain way. Listening to them is the only way.
Difficult conversations are also found in personal life, I have neglected difficult conversations in relationships that I still regret. I also have struggled with difficult conversations with myself. Is what I am working on the right thing? Am I wasting my time?
I think accepting that I am shying away from the conversations is the first step. My next is to build a real framework to have mental model to face these conversations.
Now, I seek difficult conversations. Ive had two this week, next week, I'd like 5.
That is where I will find my real growth.
March 4, 2026
Not everyone is going to make it, and that's okay.
I flew from Atlanta to Chicago to a trade show by myself to network in the industry. I got incredibly excited when I saw a company from the most famous startup incubator of all time, people like me, trying to start a company in healthcare. I was immediately drawn to their background and what got them started in the industry.
They were a group of incredibly start college grads that declined opportunities in corporate America to start their own business, founding their company in SF. My path while different was aligned with theirs and it felt like I was getting closer to creating a real network in the industry.
I could tell they were focused, and stressed. That's fine. I am too. I think the conference went well for them and we had great conversations, but they couldn't hang out in the evenings due to the pressure they were putting on themselves.
Since then, I have texted them a couple times but our communications have stopped.
I don't know if it's just me, but I tend to look people up when Im bored. Even their companies as well, that's why I had to delete social media I guess.
Today, they just pivoted. It looks like they are building in another vertical and I don't know how this makes me feel, for one I was excited to talk with other founders in this space but also does this mean this group of smart co-founders saw the opportunity or lack thereof and switched? How does this reflect on me? I worry that my stubbornness leads me down to the wrong path in building the product.
I also know that this is a marathon, as the barrier to becoming a software founder diminishes to a $20 Claude Code plan the ones that will be able to start a business won't be how smart and technical you are but on grit, taste, and execution.
I hope to see them at the next healthcare conference that they told me they would be attending.
If not, I know that meeting them was still highly impactful for me, and I wish them the best of luck.
March 4, 2026
This is going to be a stream of consciousness and might be mostly wrong. If so, you can email me. I am also a little sick, and that always affects my mental state.
Customer discovery, the most important thing early stage startups should be doing. At least, IMO. Selling in healthcare is not easy, just like selling any B2B. I'd say the difficulty of selling in healthcare is there isn't a LinkedIn for most doctors. There isn't a LinkedIn Sales Navigator to message every doctor in the area. They don't use LinkedIn.
Now, how do you talk to doctors then? I have found the best way is to ask doctors to connect you with their friends, and to make friends with them at conferences.
Cold outbound becomes a numbers game, and the numbers are poor. My sample size is small, but name dropping working at a nearby office gets me past 50% of the gatekeepers and then it's up to me that the decision maker will have the time to set up a meeting. This is in person as well.
So, what I am getting at is if it's really hard to talk to customers, and you aren't even selling anything then what percent will want to buy your product? Expanding on this point. People are generally nice, I'd say a higher percent would be nice and want to talk to you than want to buy your product.
I guess it's different if them speaking to you is them doing you a favor, but if your product is so good then they feel like you are helping them by selling to them?
Maybe it's my own insecurities, and worries about the product I am selling.
I sense a pivot coming. I feel like my design partner is doing me a favor by using my product, and I think he feels that way too. If I don't see real usage numbers yet. I know it feels like giving up early but my design partner is highly specialized so finding another one like him will be hard, and these people are doing it for free. I am narrowing down on a narrow industry to find design partners.
I read and saw that if you find product market fit the customer will buy your sales pitch 50% of the time. So, if I was selling a product that solves a real problem in the office then they would buy what I am selling 50% of the time. Let's do the numbers.
Let's say the size of opportunity in my state is 500.
So taking the average, I would be able to have meetings with 80 offices. When I speak to offices a large percent, let's say 80%, says this problem isn't significant for them. So that leaves 16 offices, and half would actually buy this product at product market fit so 8 offices. My price for this product would be $200 a month max. So, $1,600. I know this is very rough, and probably very wrong.
One thing to take note of is that my product would benefit from network effects but network effects are only strong once you are providing enough value for more users to join on the network.
I am setting a new deadline. This month, I am going to have to decide if it will be worth pivoting. I cannot let my stubbornness deceive me. The only way to figure this out is to talk to more customers. Coding isn't gonna help me anymore. That's true. I am going to have to figure out the best way to talk to customers. I am a little sick, but that's my plan.
I asked Claude to act like a famous investor and rebuke my thoughts. Here is what it said and my response:
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From: The Investor To: Benjamin Shifrin Subject: Re: On talking to customers and GTM |
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Hey, Thanks for sending this over. I read the whole thing. You asked me to email you if you were mostly wrong, so here I am. You are doing what a lot of founders do, which is building a math problem to justify a feeling you already have. You wrote an entire post rationalizing a pivot before you have even done the work to invalidate the current idea. That is not rigor. That is fear dressed up as analysis. Let me go through what I think you are getting wrong. First, your TAM math is backwards. You are starting with 500 offices in your state and working down to $1,600/mo. That is not a market size problem. That is a pricing and expansion problem. If the only addressable market for your product is 500 offices in one state at $200/mo, you do not have a startup. You have a small local business. But I do not think that is actually true. I think you have not thought hard enough about whether this product could serve adjacent specialties, whether the price could be 10x higher if you solved a deeper problem, or whether you are artificially constraining the market because the current version of the product is too narrow. The answer to a small TAM is rarely "pivot." It is usually "go deeper" or "go broader." Second, you are confusing difficulty of sales with weakness of product-market fit. Selling to doctors is hard. You said it yourself. But you are conflating the friction of reaching them with the signal of whether they want what you are building. Those are two completely different things. Enterprise sales to hospitals is brutal and those companies are worth billions. Difficulty of access is not evidence of low demand. You need to separate distribution problems from value problems. They require different solutions. Third, the design partner thing concerns me more than anything else you wrote. You said you sense he is doing you a favor. That is the most important sentence in this entire post and you almost buried it. If your design partner is not pulling the product out of your hands, if he is not asking you when the next feature ships, if he is not telling colleagues about it without you asking, then you have a real problem. But the problem is not "I need to pivot." The problem might be "I built the wrong thing for the right person" or "I built the right thing for the wrong person." You need to figure out which one it is before you do anything else. Have you sat down with him and asked him directly: if I took this away tomorrow, what would you do? If the answer is "nothing, I would go back to what I was doing before," that is your signal. But you have to actually ask. Fourth, you have not talked to enough people to know anything. You are drawing conclusions from a tiny sample and you know it. You admitted your sample size is small. So why are you making decisions? You said coding will not help you anymore and that is correct. But you also said you are "a little sick" and that is your plan for the month. Come on. That is not a plan. A plan is: I will talk to 40 doctors in the next 3 weeks. Here is how I will reach them. Here is what I will ask. Here is how I will track what I learn. Here is the specific signal that tells me to keep going or stop. You need a system, not a vibe. Fifth, stop averaging your cold call and in-person conversion rates. They are fundamentally different channels with different economics. In-person at 20% is solid. That tells me the product resonates when you can actually get in front of someone and explain it. So why are you spending 3 hours cold calling when 2 hours of in-person gets you better results and better signal? Double down on what works. Go to every conference. Show up at every medical society dinner. Ask every friendly doctor for 3 introductions. Warm intros in healthcare are the entire game and you already know this. Sixth, the 50% close rate at PMF thing you read somewhere is not a universal law. It is a heuristic and it varies wildly by industry, price point, and buyer type. In healthcare, with a $200/mo product, if you have real PMF the close rate might be 30% but with near-zero churn and strong word of mouth. Do not anchor on someone else's framework. Build your own based on what you are actually seeing. Here is what I would tell you to do: Stop building. You already said this. Good. Have 30 real conversations in the next 3 weeks. Not pitches. Conversations. Ask them what the worst part of their day is. Ask them what they wish existed. Ask them what they have tried and abandoned. Do not mention your product for the first 15 minutes. Get honest with your design partner. Ask the hard question. Record what he says, not what you hope he says. Set a real decision criteria. Not "I will decide this month." Something like: if fewer than 5 out of 30 doctors describe the problem I am solving as a top-3 pain point, I will pivot. Write it down before you start so you cannot move the goalposts. If you do pivot, pivot toward the pain you hear most often in those 30 conversations. Do not pivot toward a new idea you had in the shower. Pivot toward evidence. One more thing. You wrote "maybe it is my own insecurities." I want to be direct with you. Some of what you are feeling is legitimate pattern recognition. Your gut is telling you something is off and you should listen to it. But some of it is also just the normal terror of building something new and not knowing if it will work. Every founder I have backed has felt exactly this way at some point. The ones who succeeded did not pivot away from the fear. They ran straight at it by talking to more customers, faster, with more honesty. You are not out of the game. But you need to move faster, with more structure, and with less narrative-building around why it might not work. Go talk to people. Best |
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From: Benjamin Shifrin To: The Investor Subject: Re: Re: On talking to customers and GTM |
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Devising a structured "pivot plan" First, yes I will create a plan throughout the next couple days. I will go "pencils down" and actually figure out what my customers want and go even harder on reaching out for conversations. There have been a lot of people that have cancelled my meetings. I am going to follow up even stronger. My design partner. I will be meeting my DP in his office this Friday. I am going to really examine the product in his office and yes ask him real questions of how this would affect his day to day if it didn't exist. It is correct that he is not pulling the product out of me. But, he hasn't used it yet. I am going to come up with a plan to talk to him and have great questions to ask him. TAM: Speaking about TAM is rarely worth it since I know it can always change. However, I am not selling to hospitals. I am selling to dentist offices that are used to paying max a few hundred dollars for my solution. I need to think more what my objectives and metrics for pivoting are, but that will be my priority today. I have always told myself the last thing I want to do is make something no one wants, and well, it's time for the reckoning. |
March 3, 2026
I was leaving a conference and sat next to someone wearing a suit on my flight. He was a Mormon on his way for his mission trip to Peru for two years. There are many Mormon founders, so I was excited to hear more about their routine and what might have caused this trend.
Here are my learnings:
Rejection. Mormons get rejected, a lot. They stand in the street approaching others and get constantly told no. The 19 year old I was sitting with said he gets one baptism a month. That's a lot of rejection! You have to learn how to be good at talking to others. Their job depends on it.
Routine. Mormons have strict routines. They go to bed at 10:30 and wake up at 6:30 every day. They only get one day off, his was a Monday. Even their days off are controlled, they can't watch movies for the entire two years.
Sacrifice. They aren't allowed to drink coffee, black tea, alcohol, use nicotine products, etc. They have to leave their phones back home and are provided phones by the church that are closely monitored. They aren't allowed to use social media and the closest they get to it are shared Google Photo links that they send to their friends to interact with each other's photos. They are only allowed to talk to their family on certain days unless it's their birthday.
Support. They have medics and trained people that support them while abroad, but the man I spoke to will not be going to the dentist for two years. They are provided some goods, mostly through donations, but they expect to spend roughly $10,000 for the two years. Most of their food and housing is provided.
Appearance. They are constantly dressed to impress. They make it look like what they are doing is important.
Purpose. When you speak to them, they sound like they know their purpose in life. Unlike many people in their 20s. What they are doing takes tremendous sacrifice, leaving everyone they know to go somewhere to be rejected constantly.
Overall Learnings Talking to someone so different from me was a great learning experience. Our purposes felt very different but our actual structure for our lives were strangely similar. I yearn to move to SF to meet people similar to me, but on this flight I did find someone. He had a wildly different purpose, but our conviction to our calling was the same.