What's your backstory?

1. My entrepreneurial journey began with a pivotal decision to go all-in, something I first became familiar with playing poker. But this time, it meant dropping out of a university after three years, with just one to go, to embrace the unpredictable path of creating and exploring. Inspired by my professor sharing Steve Jobs' Stanford commencement speech, I learned to trust in the journey, understanding that going all-in wasn't just about risking it all — it was about commitment. But this time, it wasn't just about committing to see the dealer draw the final card; it was much more profound. A win would confirm everything I thought I knew, and a loss meant more than just losing what I had, disappointing and potentially even hurting those I cared about most. To start, it meant I would no longer be able to live independently off student loans. It meant moving back in with my mom, who was already living with my grandmother, and all the shame in taking steps backward that came with that.

2. Coming from a lower-middle-to-lower-class background, money has always been tight for me and my family. My parents, especially my grandparents, always expected that I would finish college and get some career like the other "successes" they would point to as examples. So, there's been a constant struggle to reconcile that at any given time, my financial instability can be a burden to those I care about while knowing that if I keep going through that struggle, when I finally succeed, not only will the rewards likely much outweigh the alternatives, but they may also provide the internal fulfilment I gain by pursuing what I feel I'm most passionate about. Choosing the path of entrepreneurship meant that money was tight, and sometimes, none would come in at all. In these times, I've been fortunate enough to have the most valuable of investors, my significant other, who's been with me through thick and thin since the beginning and managing to help me make ends meet when I otherwise couldn't. In other words, she's my #1 investor. However, every so often, I would generate revenue (I don't believe in "earning" money, as that assumes equitable compensation, but let's save that for another time) in a way that, to me, was truly fulfilling. In my early recruiting venture, that meant helping someone get a job that helped them launch their career, where they eventually landed at Google. And more recently, with Smart Connections, I got to build something that I believed truly adds value to the world, and people have confirmed that belief by not only sharing the value it's brought to them but also by providing financial support to the project when they could easily use it for free, without me or anyone else ever even knowing. But most importantly, the unwavering support of those around me has made me feel like there is only one answer to the question of whether to keep going. While I used to be fueled by the fear of being a disappointment, because of the support from the people I care about most, I'm now driven to confirm their belief in me.

3. If I had known what I know now, I don't know if I would've still done it. I thought this whole entrepreneurship thing would be easy. Growing up, school was easy. So it makes sense why so many people expected me to continue the obvious path through college and into corporate life. I thought that same ease would translate into entrepreneurship, but I was wrong. In school, I could "cram" study for a test and ace it, like a sprint. But entrepreneurship isn't a sprint, it's a marathon without a clear finish line. Initially, I heard stats like "on average it takes seven years..." So it was easy to think, "Seven years to riches, I can do that!" But I was wrong again, and crossing that seventh year was tough, and with that came another all-in decision. I had always said that I could fall back on a career in software, but now I was seven years without a job, and my experience with job boards and recruiting made me well aware that employers did not look kindly at long stints of unemployment. So, seven years in, seemingly with less money than when I started this journey, I had to decide again between beginning a new career or continuing to pursue entrepreneurship. I was getting close to thirty, and while starting as an entry-level developer in your thirties isn't unheard of, I knew I hadn't come all this way just to go back to step one. From this point, all-in no longer meant having a backup plan; it truly meant all-in. So, while the sleepless nights remained, I could no longer spend them on regrets because forward progress was the only option. It meant I had to work hard on trying more new things, potentially abandoning the project I had worked so hard on for years but was seemingly going nowhere. Slowly but surely, I moved on from what wasn't working, which I guess I thought was building some sort of job board empire, and instead tried new things with a clear focus on creating value, which led me to develop an open-source tool for individuals to improve their notes, Smart Connections.

4. It's easy to recognize that things have yet to go as I expected. There were many sleepless nights, filled with anxiety, spent regretting seemingly every decision I have ever made. I've had to make decisions that undoubtedly disappointed the people I care about most. From every time they say, "You'd be great at this job," and having to tell them no because, frankly, the resume of an entrepreneur isn't that appealing even if I did desire the job, to "I need you to drive your grandmother here," and having to decline knowing that my car wasn't reliable enough to make it happen. But while the logic behind those decisions made sense to me, I knew that all the other person heard was "no." And even worse than that, I know that the "no" made these people feel disappointed in me. So, while I don't regret saying no because the alternative would likely have meant overextending myself, possibly to the point of breaking, I do regret that I've rarely been able to effectively communicate "why" and the negative feelings associated with that. This realization, and the luck of good recommendations from a former roommate, now in the film industry, led me to explore the art and science of storytelling, an exploration I continue to this day.

5. The things I feel most proud of contributing to the world weren't hard because of the direct challenges they provided, like the time commitments and technical problems encountered while creating Smart Connections, but instead, it was the sacrifices I've had to make to pursue that work. Something I've learned that is truly amazing is that regardless of how I feel about my progress, the people who care about me don't care, as much as I'd love to tell them about the latest developments in "this, that, and the other thing." And that's important because I couldn't imagine doing hard things without knowing that there are still people who will care about you no matter what, even when you're so down about yourself that it makes seeing these people hard, feeling like you're disappointing them. In reality, not only do those people still care and love you, but I've learned that they admire your willingness to keep going. So, beyond any other benefit I've gained from choosing my path, having the ability to stop what I'm doing and spend time with the people that matter most has been the most significant benefit. When my dad was sick, there were some times when I could just go for a week across the country to spend just a bit more time than I might've missed if I was more concerned with some expectations other than my own. By breaking free of those expectations, I'm also able to live in an area that would be less than ideal if I were to continue a corporate career path, enabling me to visit my mom, sister, and niece regularly, not to mention live in a beautiful area that would be far outside my means, even with a relatively successful career, in any of the major cities.

6. It probably would've been easier to give up. Even with a modest developer salary, I could've made a million dollars "working for the man" over the past decade. But then I wouldn't have created Smart Connections, or before that, I wouldn't have spent a decade amplifying technical content for other JavaScript developers or been able to share what I've learned about the opportunities gained from working at home. If I had given up, I probably wouldn't have had as many sleepless nights worrying about how I would generate enough revenue in the first few months just to pay my taxes and how I'd catch up on my bills after that. I probably would've been able to be put on the mortgage when my significant other, I like to call her my #1 investor, purchased the condo we lived in. I probably would've been able to attend more bachelor parties and destination weddings for people I've considered some of my best friends. But I didn't give up. Instead, with all the lessons adding up, I've begun to be able to connect the dots looking backward. And even start to appreciate the thrill of uncertainty when looking forward.  

7. After all this time, I've had to change my actions and expectations. At the beginning of my entrepreneurial journey, my expectation that the end was full of riches drove me to spend countless hours building and marketing. But building and marketing, two core components of entrepreneurship, can be done in infinite ways. So I've had to change my actions, both how I handle these areas, realizing now that I can only focus on what's sustainable based on nothing other than what I've learned about myself, which can be difficult in a world where there's always someone willing to tell you what to do. So, I began changing anything that might not contribute to my success. For example, drinking alcohol is on the chopping block. I knew that even a single drink, which all too often lead to two or three more, would prevent me from reaching my goals. So I stopped. I knew that maintaining my happiness would help me be productive, so I found time to visit family at least once a month. I knew that talking about these challenges would help, so when my brother-in-law decided to venture out into his entrepreneurial endeavours, we committed to bi-weekly meetings where we go over what made us happy, what we achieved for work, and what we needed to be held accountable for doing by the next meeting. None of it was as easy as cramming for a test the night before.

8. Exploration is at the heart of my process. Everything I've done well has resulted from what I'd consider almost aimless exploration. I often see something that intrigues me, and I dive in. A couple of years ago, that happened again with the latest developments from OpenAI, which at the time was namely GPT-3. It wasn't my first intersection with AI, previously referred to as Machine Learning and Big Data, but I could tell there was something new worth exploring. This time, I stumbled across a seemingly unknown technology: embeddings. These were numerical representations of the world, and numbers always made sense to me, so I kept exploring. At the same time, I was hitting another wall with my organization. Over the years, I would go from one organization strategy and platform to the next, leveraging each until, undoubtedly, the system would collapse, and I would move to the next, each time managing to achieve a little more before the inevitable. Well, I was at the end of one of those cycles when I had the realization that led me to Smart Connections. That realization was that I could keep track of my relevant notes without spending time tagging and linking; instead, I could use AI to instantly surface my most relevant notes for whatever I was working on. And how did it work? Embeddings. The thing I just recently discovered from a period of seemingly aimless exploration.

9. I can remember the exact moment I decided that I wouldn't continue pursuing my business degree. I had just spent an entire previous semester getting "straight As" because, just before that, I was summoned to my academic advisor, someone I had managed to avoid for nearly three years, to tell me that I had to choose a major other than business. They said that I wasn't going to be able to continue in the business school. My GPA was too low. I would have to get nearly perfect scores in every class to reach the minimum GPA requirement, which I was assured was impossible. But sure enough, I went all-in that semester, and now I was sitting in one of my first actual business classes, "Entrepreneurship 101". We were watching the (infamous?) Steve Jobs Stanford commencement speech. While there are plenty of worthy takeaways, the one quote that stood out was, "You can't connect the dots looking forward; you can only connect them looking backward. So, you have to trust that the dots will somehow connect in your future. You have to trust in something—your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life." And that was the moment that changed the trajectory of my life from the confidence of a business student to the uncertainty of an entrepreneur.

10. I used to think that everyone should be an entrepreneur. However, I believe we will see more and more people starting their own companies. Furthermore, I think that many, if not most, of the companies in the future will consist of a single person, leveraging the structure of a company to gain the most equitable compensation for the value they contribute. But there's one thing that I believe to be true more than all of that, and that is the importance of doing something you believe in so strongly that, no matter the outcome, you will keep going. I was extremely fortunate to have a mom who felt this way about motherhood, enabling her to be the best mother she could be regardless of external circumstances. Circumstances that could've easily prevented her from being someone who was always there to answer my questions, support my decisions, and give me the confidence I needed to pursue goals that could easily be considered unreasonable, like committing to a software that you give away for free because you believe that providing a tool that enables others is worthy of sacrifice. As George Bernard Shaw said, "The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore, all progress depends on the unreasonable man."

What does your business do and how did you come up with the idea?

Smart Connections makes seeing your most relevant notes easy without spending time tagging, linking, and organizing all of your notes.

It started with learning about embeddings, which can be considered mathematical representations of the world. Before this, when building a job board business, my primary method for growth was curating content. The curating culminated in developing an automated system where each piece of content was analyzed using various techniques to generate scores for features, which were then used to score the "relevance" of each piece of content. The final score was a combination of these "traits" (or "features" in terms of AI/ML) and a quality score that was attributed to each trait based on the past performance of content with the same trait. In other words, it was sort of like using a primitive embedding to find the most relevant content.

From that experience, while learning about the newer embedding offered by OpenAI, I quickly recognized the potential of these embeddings and began exploring their potential with my notes.

I learned that, by embedding the content of my notes, I could write an algorithm that would display relevant content alongside whatever I was working on. As someone who takes a lot of notes, with many getting lost in sub-folders and long documents, I knew that surfacing these ideas at the right time, like when I'm working on something similar, could be a game-changer for myself and quite possibly many others.

How did you get your first 10 users?

I was about a year into my exploration with Obsidian, the note-taking application when I built Smart Connections. Throughout that year, I spent a lot of time learning about personal knowledge management (PKM) from influencers in the space, many of whom used Obsidian. So, when I released Smart Connections, I made sure to reach out to every one of those people. And while I didn't get any significant endorsement, a simple "like" here and a "re-share" there by the right people can go a long way.

I also knew there were various places, like Reddit and the official Obsidian forum, where I could re-share my initial blog post introducing Smart Connections. Once again, there wasn't any single action that made all the difference, but altogether, sharing in each of these places helped build the momentum that brought Smart Connections to over 100,000 downloads a year later.

Original blog post can be found here.

What steps did you take to confirm that your product was a good match for your customers needs?

Before Smart Connections was even a thought, learning about note-taking systems from the PKM and Second Brain communities helped me recognize that many people using these solutions were like me, all over the place. Whether having your mind in many places at once was from ADHD, the expectations of quality research, the intense requirements for world-building in novels and screenplays, or simply broad interests that have developed over time into personal encyclopedias, identifying with the struggles of all these people made me realize that I have found "my people," "my tribe," or whatever you want to call it.

So I vividly remember the necessity and urgency accompanied when I had the spark of an idea for Smart Connections. I knew that it would help me make sense of all the ideas I have floating around, without requiring yet another system for me to keep up with, well, that's the kind of thing I just knew had to be done right away because if it could help me, it would help these other people I've started relating to through my PKM/second-brain explorations.

But it wasn't for everyone, at least at first. Obsidian has a strong privacy-focused audience segment, and they sure were quick to let me know that sending all of their notes to OpenAI for processing was a non-starter. At first, as someone who previously held all my important documents in Google Drive, I couldn't understand. But their persistence was great for Smart Connections.

By the end of 2023, I was able to implement local embedding models into Smart Connections. That means sending your notes to OpenAI is no longer required for the flagship feature, Smart View, which instantly shows the most relevant notes alongside any note you're currently working on in Obsidian. Since this development, the number of downloads has nearly doubled, and the number of new project supporters has continued to grow.

How did you reach and acquire your first 100 users?

Obsidian users can download approved community plugins right inside of Obsidian. But they would have to know what they're looking for. That's where many incredible people in the Obsidian & Smart Connections communities come in. Many have gone out of their way to share how they use Smart Connections to improve their PKM/second-brain systems by creating videos, writing content, and sharing on social media. New users continue to tell me that they found Smart Connections from videos recorded by other users over six months ago!

Also, the many people who have contributed their feedback through the GitHub issues and discussions make using Smart Connections much more attractive to new users. When someone stumbles upon the GitHub, they don't just see seemingly unintelligible code. Instead, they see that Smart Connections has a thriving community where they, too, can play an active role in the future of its development.

How did you monetise your plugin?

As an early-access developer of ChatGPT plugins, I had my own personal Obsidian-ChatGPT integration that enabled the AI to interact with notes directly on my desktop. My original intention was to release this software for free. However, OpenAI decided to keep locally hosted plugins restricted to approved developers. That meant every user of the ChatGPT integration would have a marginal cost, preventing the plan for a completely free and open-source version from moving forward.

But, ChatGPT having access to my notes was still really cool and valuable, and I wanted to make that available. So, I decided to take a page from Obsidian's book and offer perks to supporters. After spending some time adapting my original plugin that ran locally to something that could run securely on a server, I provided a ChatGPT integration as a perk to supporters of the Smart Connections Obsidian plugin.

Within minutes of publishing the opportunity to support Smart Connections, I had my first few paid supporters, giving me a feeling that I can only describe as magical, which I continue to get even now when I see that more people want to support the work that I'm passionate about, especially when they could continue to benefit from using it without any cost to themselves, and without me ever even knowing!

Now, there's already something to be said about the feeling entrepreneurs get when they sell the first thing of their creation, and I was fortunate to get that starting at a young age and many times since. But, the way Smart Connections is positioned, making the income I receive synonymous with support rather than some obligation or expectation, truly is something different.

While I would like to think that everyone simply wants to support my work on the project, I know that for a large portion of the supporters, the ChatGPT integration made them decide to become a supporter. And I'm glad it did. In the eight months since initially releasing the ChatGPT integration and supporter program, I've learned a ton, and the feedback has led me to revisit my work on a more advanced ChatGPT integration, which Smart Connections supporters are currently beta testing, a software I'm calling "Smart Connect."

Why did you choose to build your plugin for the Obsidian platform and not for other platforms?

Obsidian is a platform I was using extensively, and Smart Connections began as a tool to help me solve my problem of losing track of the notes I had stashed away in my vault.
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Other platforms weren't an option, partially because I didn't use them. But it is also because community plugins are somewhat unique to Obsidian.

As for a standalone product, Smart Connections, especially at the beginning, would've had a tough time standing on its own. It made sense to have the feature as something built into the thing many others, and I were already using.

But over time, new features and ideas have come up that may be better on their own, like the new Smart Connect software for connecting your notes to ChatGPT. While currently focussed on Obsidian users, the underlying technology isn't exclusive to Obsidian and is built to be independent of it, unlike that of the Smart Connections plugin.

Who are some recommended experts or entrepreneurs to follow for learning how to grow a business?

The Mixergy podcast was hugely influential to me. There are many great resources out there, but undoubtedly, I spent more time listening to Andrew Warner interviewing other entrepreneurs than consuming any other resource. The way Andrew produced his interviews provided insights that were much deeper than how to grow a business. His formula walked interviewees through a "Hero's Journey," which illustrated the depth of entrepreneurship by walking listeners through their personal struggles and the resilience it took to overcome them. As someone who didn't have the opportunity to see what the journey of entrepreneurship looks like first-hand, a resource like Mixergy was an invaluable asset, and I couldn't say where I'd be today without it.

How big do you think your plugin/business can become and why?

I've always had this thought that goes something like, "If I can just get from X to Y, then I know I can get from Y to Z, and from Z, the sky is the limit."

In other words, I believe that if you can do any one thing well enough, particularly if it provides value and attracts others, then you're just a couple steps away from making "a one-person billion-dollar business" (or whatever otherwise seemingly impossible outcome is desired).
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The way I see Smart Connections and the surrounding business is "building tools that enable individuals to reach their goals." You could probably narrow that to "...with AI", but in a few years, I think that last part will be expected from any tool.

So the "how big formula" has to be something like $$$ = A x B x C where:

- "A" is the total addressable market (TAM) for tools that enable individuals to reach their goals.

- "B" is the total number of tools I need to develop to reach my personal goal of building a one-person billion-dollar business.

- "C" is the average market share claimed by the tools I release.

What are your future plans for your plugin?

While I've been fortunate that people support the plugin monetarily, the plugin itself began and will remain a passion project that I utilize to explore new opportunities to integrate AI with my productivity system (or whatever you want to call it, PKM, second-brain, etc).
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To better do that, I've been re-writing almost all of the code into open-source modules that other projects can reuse. There could be dozens of open-source modules in total. I've sketched out at least a dozen and already released three. This process will improve the stability/reliability of the code, further enabling me to explore ways to utilize AI with my PKM/second-brain system.

Any quotes you live by?

For better or for worse (and sorry for lack of attribution):

- "How you do anything is how you do everything."

- "Better to stay quiet and be thought a fool than to open your mouth and remove all doubt." - was on a wall in my 8th graded science teacher's classroom

- Much of my learnings can be summed up by the quote, "judge yourself for your actions but not for their outcomes."

Your links + socials

- WFH Brian‍

- Twitter‍

- Linkedin