Joseph Jacks’ Personal Blog

Through my employer OSS Capital, I’ve been privileged to invest > $1M in > 30 different startup founders across the world — all at incorporation ($15-20M concentrated in a handful of places, and around $2-4M on average in each company). Overall we’ve made nearly 70 investments so far in the last 5 years but this post focuses on the things I consider a lot where we led rounds at incorporation ($1M+ investments)…In all of these cases, I have iterated and refined my approach to reaching conviction but most of it happens within the first 1-2 conversations (many instances on the spot in the first moments of a meeting). I can also very often reach conviction on a person and idea well before taking a meeting. When this occurs, I work very swiftly at the absolute earliest stages to make myself known to that person in a respectful and friendly way.

As mentioned, I tend to reach conviction very quickly on investments and ideas. But the best kind of conviction grows on you more and more even after quickly falling in love…

Conviction is a common phrase thrown around by investors and folks in the technology/startup ecosystem.

Conviction and Belief are essentially synonyms. To be convinced of something is to believe in it.

This means that conviction is extremely subjective, qualitative and personal. It boils down to stylistic taste, one’s understanding of the current set of moving chess pieces at Micro and Macro levels, judgement of character and a wide gamut of unproven hypotheses / hunches about what the trajectory of an idea could be.

For me, I must both believe in the idea and the person behind the idea. I’ve actually never invested in just a person without deep clarity and appreciation for the idea as well.

To reach conviction about a person requires me to believe the person is absolutely maniacally obsessed with the idea they are working to manifest into reality. They can’t not do it. They lose sleep over it. It is not work, it is their purpose. They are pulled in, not pushed in. There is ZERO downside protection, because there doesn’t need to be. Failure is not an option. Period. That must come through in spades. It must ooze out of the person like bubbles ooze out of a champagne glass when you have poured it in too quickly after popping the bottle.

Belief is very multifaceted. I can’t just believe the person and their abilities to manifest destiny, to persevere, to be mission driven and not mercenary in their approach… I must also believe that the world is ready for their vision at this particular moment in time, and provided things get executed with a very high level of precision, the opportunity set is enormous — at a minimum 500 times the entry price of what I’m paying. Ideally 1,000-10,000 times.

To reach conviction about an idea, I must be able to navigate the space of the idea sufficiently to riff on the edges of it with the founder, to complete sentences, to brainstorm the roadmap years into the future, to understand how we will attract and retain the best talent for the specific quest at hand, to have a comfort level with the market dynamics that I know we will be creating or disrupting an existing industry and if somewhere in between what that would entail.. I must also be infected with the idea myself such that I want it to exist as badly or maybe in some cases EVEN MORE badly than the founder themselves.

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This kind of “idea obsession virus” must be apparent very early on in the exposure process (leaning in, understanding.. which is usually the first day or so of coming across the idea)… it must then grow on me more and more intensely over time in a visceral and compelling manner — where I’m thinking about it when I didn’t expect to .. showering .. walking my dog .. doing yoga .. or wanting to learn more and more even when time runs out or I have to reorganize my priorities. If something is worth it, you make time.

I find it impossible to reach conviction on ideas or people that are remotely zero sum. You must absolutely be positive sum in your mindset and philosophy in order to excite me. There is no exception.

People who are what I’d call “full range” or “full spectrum” are the most compelling people. This means they are deeply technical artists able to craft the most complex things with ease. World class engineers and builders. But also able to sell anything to anyone, have a charm like a horse or snake whisperer .. communication skills that also encompass the full range of personas a message would be directed to.

Perhaps most importantly, they must be humble and grounded, full of self awareness and an appreciation for the fundamental truths of life. Oriented in a way that shines light on everything they touch, brings a fresh first principles view to their work and inventions.

Additionally, people who are able to (and do) continuously learn and “level up” their skills and comfort levels to more and more complex environments they create or enter.. those are the rare few. This trait is not as critical but so powerful when it exists and can be nurtured.

Another trait I should mention as well is decisiveness. This is critical. The best founders I work with are extremely decisive and take in new data constantly, iterating on that new data and improving what they are doing very rapidly, what almost feels like in real-time. This process should be like breathing. It should not appear difficult. If there is any resistance to this or friction / slowness in this specific area … 🚩🚩🚩🚩🚩.

Also, being direct / frank / blunt in discussing things is important and very much my style, so I am sensitive to that. I am pretty good at spinning things so if I sense the mission is contrived in any way or there’s a vibe of BS in the air on the lines of the founders story or purpose, I’ll be a very quick pass.

I’m continuously improving my approach to reaching conviction. This is the first time I’m sharing how I think through these things. Looking forward to checking in again on these lines in a year or so. ☺️