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Notes and Thoughts

Coming Clean

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The content in this post is very different from what I usually write.


Throughout this piece, I share my background, how I started with Vintage Value Investing/Stock Spotlight, the lessons I’ve learned, what I’m planning for my future, and what’s next for VVI.


I will be going on a short blogging and social media hiatus. Please consider taking my survey if you would like to help me determine what to do next. I greatly appreciate your feedback.


Thank you for reading as always. I’ll see you soon.


So, What’s Going On?


Short answer: a lot.


Since I began blogging, I have been plagued by thoughts of inadequacy, fear of failure, and worst of all, fraud.


It’s time I let my readers know how I feel about these thoughts. Given that you are the ones who read my content, it’s only fair that I open myself up completely to you.


Please note that throughout the story I am about to tell, I had no malicious intent towards my readers, and did not set out to actively deceive you. I kept things private and sparse because my career and my privacy were more important to me.


Without further ado, here’s my story.


About Me


My name is Dillon Jacobs and I am 28 years old. I’m from a small town in Ohio called Mt. Orab. I lived there all my life.


After I graduated high school in 2011, I didn’t know what to do with my life. School was boring to me, and I didn’t want to go to college right away. I was aware of my laziness in school and my tendency to party.


To curb my inner party animal, I joined the Navy as a “mature” decision. Since I was a strong swimmer, I joined as a rescue swimmer.


I made it all the way through Naval Aircrew Candidate School, and most of the way through Rescue Swimmer School, when I woke up one morning and I couldn’t walk.


After a trip to the doctor, I discovered that I had severe swelling and inflammation in my left knee, which would require physical therapy (no shit!). In spite of my suspicion that I tore a ligament, I never had surgery and recovered slowly over time.


Anyway, that was it for my short aviation career. I was then re-rated to an Intelligence Specialist. After going through six months of training, I reported to my first duty station, the Office of Naval Intelligence within the beltway of Washington D.C.


For my first duty station, it was pretty cool to work at a national intelligence agency in the nation’s capital. A year later, I married my high school sweetheart. Soon after, we learned we would be moving to Japan.


May be an image of 2 people, including Dillon Jacobs and people smiling


Fortunately, I was able to land a job on mainland Japan (most people go to Okinawa…ew), about an hour away from Tokyo. Japan was an amazing experience! While I was there, my wife and I became infected with the travel bug, and we traveled as much as we could around Asia with my busy schedule.


The coolest thing about this tour was that I got to work in a helicopter squadron – exactly where I wanted to be when I first joined.



Then, in 2018, I received orders to report to EUCOM HQ, in Stuttgart, Germany. It’s been here since. Again, we got bitten by the travel bug, but even harder this time. Even with Covid, we have been blessed to visit so many countries during our tenure in Europe.


I’ve been extremely fortunate to have such an amazing career and have lived in so many different places at such a young age. My experiences in the military have been challenging and stressful, but I’ve met some of the most wonderful people I could ever hope to meet.



I wouldn’t change it for anything.


How and Why I Bought VVI


Let’s move on to the most important part of the story. It was during my time in Japan that I began to take my finances seriously. We made it a priority to eliminate my wife’s student debt while she was finishing her BS in Criminal Justice.


Through a combination of willpower and determination, we were able to wipe out her student debt in two years. I realized that I now had a large surplus at the end of the month. At the time, I began researching more about investing and doing things that made the most sense:


  • Contributing more to retirement accounts
  • Saving cash for a home (eventually)
  • DCA into basic ETFs


This is what I did until we arrived in Germany, and then I learned more about value investing. As well as watching a bunch of YouTube videos on basic concepts, I read books like The Intelligent Investor and One Up on Wall Street.


Though I was struck by the concept of value investing, I still considered myself too much of a novice to begin buying individual stocks. In the meantime, I picked up a copy of Rich Dad Poor Dad, by Robert Kiyosaki.


Rich Dad Poor Dad: Was die Reichen ihren Kindern über Geld beibringen (Hörbuch-Download): Robert T. Kiyosaki, Michael J. Diekmann, FinanzBuch Verlag: Audible Hörbücher & Originals


I was invigorated by this book. The writing of Kiyosaki itself didn’t inspire me much (he doesn’t seem to be a good writer) but the ideas and concepts that he presented did.


Being a businessman/real estate mogul by purchasing assets and not liabilities was still new to me. I wanted desperately to get into real estate after reading the book. But there was one problem: I was stationed in Germany!


The idea of buying a house for the first time in my life while living overseas was daunting (and still is) and I decided it wasn’t a good idea. However, I thought:


“Wait, what about digital real estate? I can do that from here!”


Immediately, I began looking into how to start an online business. It wasn’t long until I discovered Flippa, and I started browsing the site daily, hunting for deals.


Then, I found it.


A site called Vintage Value Investing was for sale for $15,000. I looked at the metrics, and it was bringing in ~$500-$700/month in cash flow, 7k free newsletter subscribers, and around 15k organic users from Google/month.


In addition, I got the social media accounts, which have 9k Twitter followers and 40k Facebook followers.


Daily content was also syndicated on the site. In essence, VVI was scraping content from other popular blogs (with their permission) in order to have fresh content every day.


My understanding of Google, blogging, or SEO at this point was pretty basic, and I didn’t realize how bad content syndication is for a successful blog. These were HUGE mistakes on my part.


I thought of this investment purely as real estate, but just digital real estate. Even at its lowest estimate of $500 cash flow per month, this seemed like a fantastic deal! As long as I am able to maintain the current status quo, it will mean a minimum cash on cash return of 40% every year.


That’s a big YES! The site had everything you could ask for:


  1. Great organic traffic/newsletter subs
  2. Solid cash flow
  3. A topic I was interested in
  4. A good price


In order to do this, I contacted the owner, and we discussed a possible deal. My desire to do this deal was so strong, I even scheduled a call with him while I was vacationing in Greece.


We had a great conversation. The owner started the site as a hobby and side business. After gaining some traction, he had a substantial following. Nevertheless, he later decided to pursue higher education and career opportunities, so he found it difficult to find the time for it and decided to cash out.


I decided to put in a solid bid at $17,000, or $2,000 above asking price. Neither did I ever consider this as a stock investment, nor did I do a DCF. The only place I thought of this was in the context of real estate, which for me was cash on cash.


It can’t be that difficult to run a website, can it?


Upon submitting my bid, I found out my worst nightmare: I had entered a bidding war for VVI.


My brain said:


“There is no way you are going to do this, back down.”


But my gut said:


“This is your chance to build something truly special, and if you don’t pull the trigger before it’s too late, you will regret it”.


I listened to my gut. The first bid I made was for $20,000, then $25,000…all the way up to $30,000. Double the asking price.


My bid was accepted by the owner at the end of May 2019. I now had VVI…and an empty bank account.


Part 1 (2019 – 2020)


While negotiating the acquisition of VVI, I learned how the website was monetized…and it was very different from what it is today.


Here were the primary monetization methods with their rough revenue percentages:


  • Sponsored Posts (70%)
  • Weekly Newsletter Ads (15%)
  • Affiliate Income (10%)
  • eBook Sales (5%)


Everything sounded great! The former owner of the site wrote evergreen content that was complemented by free daily syndicated content. I could kick up my feet, publish some guest posts, send out a few emails, and rake in a cool extra $500/month.


Great, right?


The guest posts alone generated at least $500 per month, and sometimes even $1,000. I was exceeding my $500 per month target with ease.


Things were good! Or so I thought…


Part 2 (Covid – Present Day)


Covid began unleashing across the globe in March 2020. We were right in the midst of the Covid crash when quarantine was started, so the stock market was also at a record low. VVI’s traffic started picking up while people were locked up at home and curious about the stock market.


In the midst of people becoming more interested in the markets and I had just bought a website about investing, what a perfect time for me! For a couple of months, VVI enjoyed a significant increase in traffic and guest posts.


Then came May 2020.


While still in the firm grasp of the Covid lockdown, Google decided to update their search algorithm in May. If you aren’t aware, Google usually updates their search algorithm at least once, but sometimes twice a year.


After these updates are deployed, the internet usually goes into a tailspin for a few weeks. Experts in search engine optimization scramble to figure out what Google is prioritizing most this year so they can balance their statistics. The benefits of these updates can vary from being extremely beneficial to being downright catastrophic, depending on the site.


Guess which one it was for VVI?


Yep, down-right catastrophic. During the course of one day, my traffic declined by over 50%! Where did I go wrong? Why had Google punished me?


My frantic search for SEO research begins at this point. As it turns out, Google doesn’t like duplicate content very much, and it knew what my site was up to. Thousand of eyeballs were lost when the hammer of punishment fell.


What should I do? I didn’t know. Fortunately, VVI still had a solid reputation with advertisers, so I was still making money with affiliates and guest posts. However, I knew my current business model was not sustainable.


I had to pivot.


Coincidentally, I discovered Substack during lockdown. As a result of the pandemic, people were stuck at home with nothing to do, and the platform took off. Publications popped up like weeds in an unkept garden.


This is when I started to really notice the amazing power of newsletters and subscribers. At this point, I had gained around 1,000 newsletter subs, with the total now sitting around 8,000.


I thought:

“Wow, if I can convert only 10% of my free newsletter subscribers into paid subscribers, I could have a really impactful and sustainable business!”


This line of thinking is not incorrect, in fact it’s very lucrative. I don’t think I need to explain the amazing concept of subscription based revenue to you.


With this thought firmly implanted into my mind, I set out on my journey to revamp VVI. I focused on learning two things during 2020:


  1. How to properly create content with proper SEO
  2. Create a solid plan to create content that people would pay for


But there were problems.


The Issues


Firstly, I now knew I had to create organic, fresh, and high quality content. That takes a lot of time and effort. I was willing to put in the work, but now the entire investment concept had changed. I had to invest FAR more time into VVI that I had planned.


But I sucked it up. I thought:


“This is a actually a good thing. Instead of acting like a blogger, I can actually be one.”


I’ve always enjoyed writing, so I accepted this problem as a challenge. I actually began to write content on a weekly basis. This was mainly directionless or relatively uninspiring thoughts, but it was something.


I had begun to write. But onto the second problem…


In order to convince people to pay for high quality content, they want to know the source of that content, and if they can trust it. This is 100% legit.


I was not keen on revealing myself on the internet for a number of reasons. Upon the purchase of VVI, I had planned to build up more of a brand than a singular blogger identity. I wanted people to come to the site for the name, not for me.


Why? Well, mainly I worried more about the security implications it had on my job and security clearance. While it’s certainly not forbidden, the military/government does not prefer you be overt about the things you do and say on the internet.


If you are not familiar with the term OPSEC (Operation Security), then you can read more about it here. This was my primary concern on revealing my identity.


However, I learned a very important truth:


When it comes to most internet content, people always prefer to consume content that is more personal and comes from an individual that they can understand, trust, and identify with.


So, in order to sell premium content, I first needed to sell myself. This was a fact I had to get over if I wanted to create success with VVI. I spent a lot of 2020 mulling this over and reaching out to other bloggers and creators to see if this was the right path for me to take.


In the end, I decided this is what I had to do in order to succeed. I spent the rest of 2020 and some of 2021 with the intent of building more trust with my audience and create weekly content that would be engaging.


Throughout my build-up phase, I noticed that writing “deep-dives” (this phrase has been absolutely murdered by the community BTW) was immensely popular content, especially on Substack. So, I tried writing more about specific stock research on VVI.


To my surprised, I loved it! There was something immensely satisfyingly about researching a company, compiling the evidence, and presenting your case to the world. I decided that this was the kind of content I wanted to create.


After more rumination, I decided this would be my content plan:


  • Move the weekly newsletter to Substack and create Stock Spotlight
  • Create two premium research reports per month (24/year) for paid subs on VVI
  • Write one free shorter article per month on VVI on value investing ideas


There were logical reasons for these decisions. At this point, my weekly newsletter had risen to 9k subs. This is great, but expensive! A newsletter of that size was costing me around $100/month with Mailchimp. The move to Substack made sense for two reasons:


  1. The refreshed and rebranded newsletter was on a platform that better served the content
  2. It was free!


So right there, I was saving $100/month out the gate and putting my content on a platform where it would be more visible. Score!


Regarding the premium content, I felt like two 24 reports/year for $200 was a good value for what I was creating. But I didn’t think too about the content itself. I was just more concerned about creating research that someone felt was good enough to pay for.


The free article on VVI was mainly just to keep the site up to date and fresh looking, as well as explore any ideas I had.


In hindsight, this was a monstrous amount of content production for one person with a full time job. When I consulted some of my other blogging colleagues, many of them warned me that this sounded like too much. I shrugged it off, thinking that I could manage. It would all be worth it if I could get enough premium subs.


With the plan set, I launched Stock Spotlight and refreshed the site in late April 2021.


How did it go?


According to the numbers, I thought I could easily convert 200 free newsletter members into premium subs. Boy, was I wrong.



Even with a discount code, I gained zero premium subs upon launch. Zero! A week went by, and nothing happened. I was dumbfounded. How could not 1 person in 9,000 not even be interested in my content!


Despite the shock, I continued to follow through with the plan. Throughout the summer, premium subs started to trickle in slowly. This was a good feeling, but I was still bummed.


I’m now up to 15 premium subs and am gaining (on average) 1 premium sub/week.


Additionally, over the summer I started to become much more active on Twitter. I had pretty much neglected social media for the most part of my blogging journey, and I realize this was a HUGE mistake.


Twitter and social media (but specifically Twitter) has been a huge resource for me in researching new ideas, connecting with other creators, and marketing myself to the world. While it can absolutely be a source of toxic and polluting ideas, it has brought me tremendous value.


Personal Stuff

So, why am I writing you this? If I am slowly but surely gaining premium subs, shouldn’t I just keep my head down and press on?


Well, yes, and that is what I have been doing for months now. Throughout this entire period with VVI (but mostly since I started writing for myself on VVI and on Stock Spotlight) I have had two nagging concerns rattling in my brain.


Imposter Syndrome

Since I purchased VVI instead of founding it, I feel like I cheated. I bought an audience and inherited ideas that I didn’t create myself. While I (mostly) identified with these ideas, I did not create them on my own.


I feel like a fraud.


The more and develop myself as an investor and writer, the less I come to identify with a single minded concept that is “Vintage Value Investing”.


Do I still identify as a value investor? Honestly, I don’t know. I don’t really want to identify as anything but myself. I don’t want to be put into a box.


Throughout my learning experience over the year, my thoughts and opinions have changed, but my platform does not necessarily allow for that change. This is a huge problem for me as a creator.


Exiting the Military


Next summer, I will be separating from the military after a decade of service. This decision is best for me on a multitude of levels that I don’t want to dive into here, but basically I am just ready to move on to something else.


I’ve been planning my exit for a while now, knowing that this tour in Germany would be my last stint in the Navy. I felt like I was under pressure to get a solid business plan underway before I separated, so I could just slide right into full-time blogging after I get out.


Honestly, I would love nothing more than for this to happen. But I put too much pressure on myself, rushed a premium launch, and got too carried away with my dream.


So what’s the plan upon separation? College. On top of work and blogging, I have still somehow made time to complete my associates degree (like literally a week ago, lol). I plan to use my GI bill and complete my bachelors in finance…maybe?


Not sure though, still thinking on it. Open to suggestions!


How will we make money? Well, the GI bill will cover our housing expenses (which is awesome!) But it’s time to allow my wife to take the reigns and let her be in control of here career for once. I’ve been stealing the show for far too long, dragging her across the globe with my career, so it’s her turn to shine.


My wife is currently on a job hunt for a employment back in the states. This is tremendously stressful for her, as job hunting normally is tough, but overseas is a whole other beast. She’s been through multiple interviews, but still nothing yet.


We remain hopeful, but its stressful.


What’s Next?


Usually, when I write Stock Spotlight, I set aside a Sunday morning and write after researching throughout the week. I tend to usually write better in one sitting in one stream of conscious thought.

Last week, as I sat down to write my issue on IMXII got a feeling that I was hoping to never feel.


The feeling that writing was a chore.


Most of the time, writing is an enjoyable experience that I look forward to. It feels great to release your thoughts and ideas to the world. But last week, I felt as if I was doing a chore, akin to cleaning the toilet.


This is when I knew I was burnt out. Something needed to change. Unfortunately, it’s just not feasible for me to continue to work full time, go to school, write content, market myself on social media, and support my wife and focus on our transition.


This was hard for me to process, and I have been pondering all week on all my thoughts and feelings I have just mentioned to you. I have been producing so much content that I feel like I am not able to properly ingest enough material to keep up.


I miss reading hedge fund letters. I miss reading books. I need to get my inspiration back.


For this reason, I will be going on a short hiatus from blogging and social media.


I say short, but quite honestly, I don’t know how long I will require. I really do enjoy blogging and writing online and sharing my opinions and research with all of you. I don’t plan to stop completely. But I have to do so sustainably for my health, both mentally and physically.


I also need to establish my own dialogue and inner voice separate from VVI. This may mean that the name and brand of VVI may go away completely. I have not decided yet, but just know that I may not come back under this moniker.


The only content I will be producing during the hiatus are the research reports for my premium subs. I have made a commitment to them, and I refuse to break that commitment.


Premium subscribers can rest assured that premium content will not stop during the hiatus.




I have had some great feedback from some amazing creators like Andrew from Yet Another Value Blog (@AndrewRangeley) and from Sven Carlin (@SvenCarlin) on my content.


Andrew let me know very honestly that my content was nothing special, and was “paint by the numbers”. At first, I was a bit miffed, but I then noticed something.


He was right.


I wasn’t adding any new insights or information. Just simply regurgitating facts that I had found. That’s not good content. I’ve gotten better, but still have a ways to go.


I had the pleasure of meeting Sven Carlin last month in Slovenia while on a trip there.


He let me know he was unconvinced about my value proposition to readers, and told me he would not subscribe himself as a reader. I told him my of my grand plans of building a platform for VVI, and then he stopped me in my tracks and bluntly gave me one piece of advice:

“Provide value for your audience.”

So, that is what I plan to do. I am going to go back to the drawing board, and develop a new plan that is more sustainable, and something I can grow into. I want to provide value to you, dear reader, and do it in a way that reflects my own values, and nobody else’s.


That probably means less content right off the bat. But I am going to take all the lessons I have learned and put them into action to create the best content I possibly can.


To do so, I have created a survey. If you are interested in helping me formulate my thought into action, then please consider taking the survey. I value all of your opinions greatly!

Thank You


Thanks as always for reading. I hope to see you all again soon.


And I’m screaming at me
Slow down – I keep losing my way
Find out – I keep pushing away
It’s so hard to believe in myself

– Born of Osiris, Shadowmourne

About me
Dillon Jacobs is the owner and lead editor for Vintage Value Investing. He is a passionate value investor who believes in the fundamental principles of Superinvestors like Warren Buffett, Charlie Munger, Ben Graham, Peter Lynch, and many more. His career has taken him to many destinations around the globe, and he has lived in both Asia and Europe.

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