These are check-in emails I send to entrepreneurs I admire to keep myself accountable on my startup journey.
Good afternoon,
This is what I said I would do:
(Outreach every day)
Additionally, I went in person to a couple offices, started working on creating some partnerships with other vendors as well. I slowed down on coding, really focused on systematizing outreach so I can sell more. When I work on something I now tend to ask myself, will this move the needle for me? That's really helping me prioritize.
I was able to learn a lot on what methods work for cold outreach. So here are updated methods:
Before I get to what keeps me up at night:
The last couple days were difficult for me, I had a realization that my revenue was trending toward project/consulting and I still didn't have a product. However, I have great news. I was able to put together the pieces of what I was selling as a service to offices and am 70% towards productizing it with the goal of 100% in the next few days. This is really exciting to me and I know people would pay for this since they paid me to do it. Now I am close towards automating myself!
Good morning,
I am going to continue to pre-sell. I will try not to show any products on the intro calls so I don't deter the customers by not having the product they want. This is how I am going to pre-sell to 5 customers.
Pre-sell strategy:
I signed on two customers. I continued the strategy shown above, and optimized it. I think the mantra work smart and not hard is something I like to say but not actually follow. So, I started looking at what strategies were working. One of the things I was most proud of because it was hard was going in person to offices. I "felt" like I accomplished a lot. I also felt like what I was doing sounded similar to the entrepreneurs I heard on podcasts like ZocDoc (who went to a bunch of offices to sell themselves). But, my conversion rates in person -> sales calls were not strong. I'll tell you why.
I wasn't selling to decision makers. I would normally "sell" to the front desk person, leave my flyer/business card and leave. When you are selling to the SMB, selling to the front desk and hoping they are gonna sell you to the decision maker + a low ACV doesn't make a ton of sense business wise. Also, not great conversion wise.
So, I honed in on referrals and my other outbound methods. I saw stronger results from them anyway.
I also went to SF, that is why this is a 3 week check in and not a 2 week check in. My trip there has finalized my decision. By the end of the year I am going to move there. I should have moved there three years ago anyway.
I haven't been coding much. I use Claude Code to build me a quick demo/MVP for a meeting and build the final product after. It just makes more sense this way. I think I wasted a lot of time vibe coding shit people didn't want. I even downgraded to the claude code pro plan, but the token inflation has gotten so bad that MAX is required for any actual development.
I started focusing on what really matters. Normally, for the past 7 months, on Sunday I would write down everything I need to do for the week. It would normally be at least 30 items. I have been doing this for the past 7 months now, and I looked back at that time and TBH, it hasn't been successful.
What if I don't need to do all 30 things for the week to be successful? What if it's just one or two things that I should devote my attention to? I was so proud I would organize my days into coding + outreach + side things + other side things. Now, I just have a system and a checklist. Did I follow this system for sales outreach? That's it. Not if I did all 30 things. Did I do the one thing that actually mattered.
Even though this email is also not related, it is good to continue them.
Another thing I did which helped me come to this conclusion was meet with a fellow startup founder in SF. We talked about what I was working on and he asked me to show him my calendar. I did and still thought to myself, "what am I really spending my time on". Is it really moving the needle? I started tracking what I did every 15 minutes afterwards. I think this was helpful and I did it for a few days so I could understand what my actions are showing are important to me. I stopped doing it because I got what I needed out of it.
I also created a system for outreach which connects me to doctors so I can do intro calls. This is a work in progress.
A side thought I have is one of the funny things about building a startup, is normally the thing that will help me move the needle is the thing I normally want to do the least. If I write down what I least want to do today and just do those, it will be a successful day. It's pretty funny.
I am going to continue this system to sell.
This is what I do everyday:
Build the product for current customers as needed.
Good evening!
I am going to continue to pre-sell. I will try not to show any products on the intro calls so I don't deter the customers by not having the product they want. This is how I am going to pre-sell to 5 customers.
Pre-sell strategy:
I was not able to pre-sell to 5 people. I have a couple in the pipeline. But, that's not good enough. I went to around 32 offices in-person, cold called about 30. I had four sales calls, started a cold email campaign, messaged just about everyone in my network to meet, DM'd over 200 on FB, I also went to a conference.
Reflecting on the numbers above, my in person + cold-call numbers should be higher. The last product I built, I built something for a few months and realized that no one wanted it afterwards. I am trying to do the opposite but I think I might be swinging in the other direction too hard. I am going into sales calls without a real product now.
I really wanted to find the best channel or channel blend for my pre-sell outreach. I would categorize them in three ranked buckets:
I would prefer to work smart not hard, FB DMs might be the best channel. I am going to optimize the texts I send. As long as I am getting meetings, it's the easiest and less stressful.
I am going to continue to pre-sell. I will try not to show any products on the intro calls so I don't deter the customers by not having the product they want. This is how I am going to pre-sell to 5 customers.
Pre-sell strategy:
Book I am currently reading: Think and grow rich
Good afternoon,
I didn't exactly meet the goals of what I set out to do the last two weeks. The reason behind that was a PMF problem, and not a me problem. Ultimately, I pivoted. Turns out the problem I was solving wasn't that big.
I found this out by trying to sell to around 8 customers the past couple of weeks. None of them mentioned I was solving a problem. I know that's a small sample size, but my customers are quite specialized so the combination between a small TAM and the size of my market made me pivot due to a combination of gut feeling + metrics I was aiming for.
I definitely made a lot of mistakes in the past with my strategy/approach which I am to fix currently. I didn't talk to enough customers and ultimately I asked my DP if they would pay for my product and they said no. So, a few days later I pulled the plug.
I found other channels to pre-sell, and actually enjoyed going door to door in offices trying to sell my product.
I went to a conference, which I am thinking is becoming more and more of a waste of time. Especially, because I have built a pretty good network at this point. I can use them instead of cold approaching people at a conference.
I found patterns of what my customers wanted. Normally in the sales call I would talk about their business and their problems. They kept on asking me to work on something while I was building out this product. I guess I just needed to take a break to listen to them to find clarity.
I also found a customer discovery question I love. Not the "waive a magic wand shit" or "what are your top 3 pain points". I like to ask "What metrics are you measuring". Anytime someone is measuring a metric, if you can build a product that pulls a lever on that metric, that is how you find PMF.
I am going to pre-sell to 5 customers before I build the product.
I am going to do this by leveraging these channels:
Thats my only priority.
Book I am currently reading: I am not reading anything at the moment. I did start a blog, benshifrin.com
Good evening!
In my stage there's only two things that matter, talking to customers and building the product. If what I am doing isn't related to those two I am not being productive. I went to a trade-show for 5-6 days which is great but my trade-show strategy is not strong especially because I don't have a booth. I mostly cold approach other guests. However, I built out stronger connections to the vendors.
I did a lot of cold outreach and learned more from that than anything else. I also coded and built out the necessary features, but that's not hard anymore. I am coding features as I am typing this. AI has made the value of code cheap. I saw that total github contributions were up 40% last year, which I believe is closely attributed to GenAI.
So, I can say I have been talking to customers and coding. But, I am missing the feedback loop that is necessary in building the product, so I will be asking my DP to work side by side to see it in action, hopefully sweetening the deal with free lunches and introducing me to his contacts to find more DPs.
My main focus is more design partners. To get this I need more conversations with decision makers.
Easiest way to get conversations with decision makers is via referrals or direct connections.
Bottlenecks: Not utilizing my network enough.
Cold calling offices shows grit but is not effective. It shows I want to talk to customers but I am not doing it in the most optimized manner. I will need to utilize my channels and my network to get to decision makers to find more DPS.
Book I am currently reading: Steve Jobs by Walter Isaacson
Good afternoon!
Software: I said: "software would be fully implemented into the client's office". Yes, I'd say I implemented Phase 1 of the software fully into the client's office. Phase 2 is not, and it is my main priority to have it completed by next-week. The next two that I cannot say with confidence that were completed are: "get client to use software at least once a day", and "software to be used in at least 3 of his partner offices." This is due to the hand-off to the client being yesterday.
Sales: I said "Generate 10 leads" I definitely did not generate 10 leads, I'll have to come up with a better strategy to generate my leads which will likely be cold outbound. I said "Network with conference organizers. I aim to be a speaker at the following conference." I did network with the conference organizers and there is momentum in me speaking. However, this does not get me closer to selling so it is something I am recognizing should be on the backburner.
Check-In emails: I did not send the check-in email like I said I would. I thought I'd put it on my calendar. I will now. The next email will be February 28th.
I can separate at a high-level of what I am doing into two parts, with my bottlenecks:
Making: I continued to build out the software. I made a lot of progress, and it is much closer to what I envisioned. My next phase is firmly on testing PMF by looking at user data, talking to customers, and by adding the main feature of my product, which I am aiming to complete by next Monday.
Bottlenecks: Time and focus are the main reasons why I have not fully shipped my software. With GenAI, there is no excuse for me to not have it completed by next week.
Selling: I went to a conference, which is great for developing relationships which could turn into Design Partners, but besides that I think it might be more beneficial for me to find PMF in other ways. I am going to lean on my connections for intros.
Bottlenecks: Fear, being scared of rejection. Lack of focus. I think I had poor strategy. It is paramount that I find more design partners and build out more pilots, my goal is to have 1 more design partner by next week.
Quote of the day: "What would you do if you weren't afraid?"
Favorite book I have read this year: The Everything Store: Jeff Bezos and the Age of Amazon
Happy New Year!
I am going to separate what I said I was going to do on December 4th in 2 parts.
Sales: I said I would go to a dental conference to obtain more leads, which I did. Around 3 people, okay for a one day event.
Project: I obtained sign off for my product in a few orthodontic offices after my meeting with an orthodontist. Something I am proud of.
After getting my first yes for implementation in an office, I took about a week and a half to build a demo using AI that I could show the doctor. This was definitely the easy part and for now, the greatest strength of vibe-coding. The ability to generate interest from a local demo to customers is unmatched. Jeff Bezos likes to have his product presentation in the form of "press-releases", Steve Jobs likes product demos, I can foresee the future of product presentations being vibe-coded projects.
The real work begins after showing the vibe-coded version. I have not used AWS before, so I have been spending the majority of my time moving my codebase onto AWS, since I am building a HIPAA compliant platform with the potential to scale. It just seems like the best fit for me. I have gotten to the point where my project is 60% of the local demo that I vibe-coded. I upgraded my Claude plan to MAX, I just kept getting rate-limits and there is no comparison to Claude Code on the market. Codex is really-really bad, like delete your dev database bad (yes it did that once).
I have changed my approach and from a bird's-eye point of view this might be the one that looking back strategically I will debate. In the beginning of December, when I got the signoff for the first implementation I was excited. However, one orthodontist saying "yes" to my project doesn't mean other people would buy it. So my next thought process was that while building it I would continue to talk to more customers. So, I spent a lot of my time networking and cold-calling. You likely see where I am getting at, I had to make the trade-off of building vs talking to my customers which did lead me to have "progress paralysis". I wanted to build, but I also was uncertain if it would scale.
After talking to friends, they made me think more if this was the right decision. I go back to what Jason Fried told me: "My advice is to go make something and then go sell that thing you've made. There's no greater lesson than doing the work and trying to sell it to customers.". So, I am focusing my priority on getting the product in the ortho office. Then doing sales and marketing. I do not want to get stuck on asking the customers if I have product market fit. I want to build the product and ship as fast as I can to determine PMF.
I think my biggest problem then was that I was listening to the YC advice that you should talk to customers before you build the product to see if they would buy your "fake" product before you built it. There's a couple things there and I think they are making a great point but I have to also ask myself how many customers is "enough". As a solo-entrepreneur doing one thing means sacrificing something else.
There is this concept at Amazon called "single-threaded leaders". At Amazon, when they have a new initiative or focus, they delegate leadership to have only one focus, which is that product or initiative. Building this business, I want to adopt this mindset as much as I can.
I need to be more consistent with these emails. I know it has been over a month. My aim is for the next one to be in three weeks, Feb 2, 2026. By the next email here are my goals:
Project Goals:
Sales Goals: I will be going to one dental conference at the end of this month. Here are my goals at the conference.
I said I was going to create the next project that is similar to Overjet AI and Pearl AI. I believed this was going to increase our patient acceptance, but could only test if it worked in our office. I ran into a wall. Our files on our server were encrypted in some proprietary software owned by Dexis, our X-ray imaging company. I did fake sales calls with Overjet AI and Pearl AI so I could understand how they decrypted the image files but did not find any success. I got them to send over some technical documents under the guise of "our IT guy needed them". Still, no success. After that roadblock I began to rollback this project since I also felt that the market is too saturated, and felt like the technical roadblock was too high. I did not want to ask any of our connections because connecting to others servers built in 2002 is a recipe for disaster (without trying it on our own). I still think this project will be very successful, and I will likely see it adopted by one of these other companies soon.
Regarding the referral platform, I have done enough validation. Even with our new initiatives and scripts, the ROI did not feel large enough to reliably sell to other offices. It is still in use in our office today, and I will continue to gather more data. However, this project is not something I believe I can scale.
Man, what did I not do? Pivot, pivot, pivot more. I know from a birds eye view this is not a straightforward process. But, that is what I signed up for, and I know that. I continue my work in the dental office trying to innovate on our processes. I also made sure to use our connections. General dentists are not the only market I can sell to. I began speaking to all of the specialists we refer to. That is mostly orthodontists, periodontists, and oral surgeons. Selling to them would be easier than general dentists because paradoxically, general dentists are pretty cheap. I know that from my own experience. Working in the front of our office I believe I found a way for specialists to strengthen relationships with general dentists.
I built the first prototype. So, I began trying to pitch it to multiple offices, none of them bit. I even sold to large oral surgery offices that are considered "enterprise > $100M in revenue. This was very naive. There is a saying, sell something people are used to buying. What I am building is a somewhat new category. I also learned various sales strategies. The process of cold calls to discovery calls to sales calls. Also, the importance of knowing who I am selling to. Initially, I was selling a solution to bring in more patients. So, I thought I would sell to the marketing people. Turns out, they are not the decision makers. So, I went straight to the real influencers, the Doctors. They become my influencers and connect me with the decision makers. It is a much better strategy.
So, after pitching to every specialist we refer to and them saying no. BTW my google slides are full of wasted pitch decks haha, I began cold dm'ing specialists in our area off of instagram. One said yes, I went in so I could sell the implementation of the product. I will likely do it all for free and have him pay me a monthly subscription if it works. I sent over the proposal document and I hope he will say yes. I also set up another meeting next Tuesday with a periodontist which is at 6:30 am.
I have another conference I am going to tomorrow. Now that I know how sales works, this will go a lot better. I will make my intro, give them business cards, and set up a discovery call ASAP, and I mean ASAP. I can't tell you the amount of people that have ghosted me. It's not even Halloween! Once this orthodontist agrees to the project scope I will begin building the first phase of the project. I set some optimistic deadlines, and I will meet them. Some people are already living life like 2025 is over, this is just the fourth quarter.
I hate selling to doctors. I suffer from insecurity already, all this comparison bullshit. Now, I have to call people "Dr" and kiss their ass.
Definitely HIPPA. I haven't built a HIPPA compliant project yet. Thankfully what I am building so far should be straightforward and not a complicated architecture, yet. If I am seeing larger adoption, I will absolutely bring in a team since growth and building is not something I can handle myself.
I said I would ask patients to sign up for the software and I asked some but not enough. I believe to get this product to work I need to get much better at sales. So, I built a sales script and a better way to increase the chances of a referral.
I like to say it is the most advanced referral platform in dental offices in the world, but I need to see success.
Outside of the platform, I have been speaking to more dentists finding their problems. I have been constantly iterating and finding new techniques to motivate our patients to refer.
While I am validating the new platform idea in my office I will be working on another project that will increase our treatment acceptance that is similar to Overjet ai and pearl. I think this has a lot of opportunity as we are seeing many patients leave without obtaining sufficient treatment. For next steps I will continue to ask patients to sign up for the platform and begin training the ML model to increase patient treatment acceptance.
HIPPA challenges, security with AI code, going back to the desk job, still living with my parents, caring what others think.