I'm Joseph Jacks, founder and general partner of OSS Capital, ask me anything!

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I founded OSS Capital, a venture capital firm which invests exclusively in commercial OSS (COSS) startup companies. We were also the lead investor in the DEV seed round back in the fall and have been partnering with the team here to grow as a leading COSS company.

I also founded KubeCon and have been involved in the Kubernetes project since the early days and open source software in a variety of roles.

Ask me anything.

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Hi Joseph, thanks so much for doing this AMA! Do you have any advice for a developer who's new to open source? I've wondered often how OSS teams manage pull requests, roadmaps, and sourcing contributors, but the furthest I've gone into OSS myself is a single pull request.


Hi Anna! The wonderful team at GitHub (a COSS company) put together this resource: opensource.guide/starting-a-project/

Hope this helps you on your journey into the exciting world of OSS!


IMHO it's ironic that GitHub preaches about the superiority of FLOSS but then ... doesn't make GitHub itself FLOSS. Like wth.



I'm curious about your thoughts on a couple failures in commercial open source that come to mind for me:




Hi Joseph! I know commercial open source ventures tend to center a lot on SaaS and web/devops frameworks, but have you seen anything commercially viable or interesting outside of web-developer-targeted open source software, or any movement towards commercial open source hardware?


Hi Joseph!

Do you work with many companies that are not yet COSS, but intend to open-source their software? I feel like the discussions involved in making a company COSS from the beginning are different from the discussions about transitioning into making their existing products open source.

I'm wondering if you have any thoughts on the differences between the two situations, and if you have any tips on how to more effectively dissolve friction from people who are feeling like they'll lose existing value if the code is made open-source?


Hi Joseph,

Thank you for doing this AMA! How do you see the Kubernetes landscape evolving in 2019? Last year seemed to be about Kubes-as-a-Service offering from multiple cloud providers. Do you think eventually the easiest play will be to not roll your own cluster, and use the hosted offerings?


Hi Joseph, thanks for doing this AMA and KubeCon! I'm curious as to what criteria you use to evaluate the feasibility of COSS startup. Are there specific attributes you look for as an indicator for success?


Hi Joseph, thanks for doing the AMA. I'm curious what makes a potential COSS a good investment for your company? I can think of stuff like solid tech, community involvement/popularity perhaps, but I'm sure the list is longer than that 😉


Hey Joseph, I'm curious about your thoughts on the relationship of security and OSS. On the one hand, the "many eyes" philosophy suggests that OSS is a boon to security, while incidents like the Equifax breach suggest we are still faced with problems in this space. I'm personally hopeful for more sophisticated vulnerability scanning technology as a solution, but I'm curious what you think.


Thanks for doing this! What are some common misconceptions about COSS?


Hi Mac! I'd say the biggest misconception is that "there is no open source business model". While OSS itself is certainly not a business model, I believe there are several business models that COSS companies implement - that work well, some better than others in many situations. Empirically, over the past 15 years, "open core" has proven to work the best, but it is not a binary thing like most frame it. It is a spectrum/gradient. More here: medium.com/open-consensus/2-open-c...


When we were investigating the pros and cons of going fully open source and leaning into the business, I definitely found a general sense of closed-mindedness towards the types of business models available for companies built around open source.

Since we're consumer-facing and fairly atypical in that sense, it was even less talked about. But learning up on the common thought patterns like open core, etc. really gave a good jumping off point for thinking about the whole thing.


Hey JJ, thanks for taking the time to join us. My question—

How do you explain how/why "open source software eats everything" to someone who is not very tech savvy?

I spent plenty of time over the holidays talking with friends/family about DEV being open-source, so I'd love to hear your approach and major talking points when talking about the opportunity of COSS.


Hey JJ! Thanks for doing this AMA. What advice would you give to a newer software developer about getting involved in commercial open source?


Hey Ali! Getting involved effectively depends on what your goal is, but diving into the exciting and hyper-growth world of COSS as a new software engineer could be helped by a couple things, I think:

1) Learn about some of the largest and most successful COSS companies that build large software product businesses fundamentally on specific exciting OSS projects! This can serve to offer perspective on the business side of things and the general magnitude of the space at least at the higher end. To support this, I'd encourage folks to look at this spreadsheet: oss.cash/

2) Read Heather Meeker's book "Open (Source) for business": amazon.com/Open-Source-Business-Pr... -- we are deeply honored to have Heather as our founding partner at OSS Capital.


Oh awesome! Thank you so much -- great resources!


Hi Joseph!

I've been super interested in the work you're doing at OSS Capital and I've been thinking a lot about the space recently and how our current market still has an enormous favoritism towards closed source products. What metrics/tools/approaches should a current closed source company (any size from the small startup to Microsoft) use to evaluate what parts of its codebase, if any, should be opened? Thanks for doing the AMA!



What are considerations around open source in terms of international expansion?

How does open source make international relationships more feasible? (Or less so in any way)

How do organizations typically think about enforcement of licenses in different markets across the world?


Thanks for doing this JJ.

Has your thesis or expectations changed at all since you officially started OSS Cap?

What has gone as expected and what has surprised you?


Hi Ben! Thanks for having me.

Our thesis has remained the same: OSS Capital focuses exclusively on investing in and helping COSS companies.

I have, however, learned a few things over the past few months in our infancy:

1) The world is still far from understanding the magnitude and profoundness of COSS as a highly categorizable thing. We have a lot of educating to do, even with $70B+ in COSS M&A/IPOs/PE events in 2018 alone.

2) The world is still far from looking at COSS from a data-driven perspective and making conclusions from that data. A lot more people need to see this spreadsheet: oss.cash/

3) The COSS category is likely to be $10T+ (trillion) over the next 15 or so years. I originally thought it would be somewhere around $3-5T, but it is much bigger than that. I plan to blog soon on (conservative) data projections to support this.

4) There are far more COSS startups out there than we can invest in (even the absolute best ones at the earliest stages). :-( ... This is only true because we do not yet have billions of dollars to directly invest ourselves (this is a function of how large the COSS space is and our age), but stay tuned over the coming future! Constraints breed innovation!

5) Our thesis has only gotten broader and more expansive: software ate the world, OSS is eating software, OSS is then eating everything else: cloud (Kubernetes), hardware (RISC-V), etc... It is even more exciting on a daily basis to have the privilege to help founders build and grow the next leading COSS companies!


A lot more people need to see this spreadsheet: oss.cash/

Looking at the chart, I see clearly RedHat dominating the market, generating half of the outcome. Why should I - as an investor - put my money in other companies than RedHat?

Don't get me wrong on that: I love to see more money being put into Open Source companies - I even work at a OSS Shop (we built among other things GPG4Win, the windows integration for GnuPG). But I see, that being Open Source comes more with a price, than it helps.


From our perspective, commercial open source has become more interesting and viable in the market in the past year or so.

It's hard to say if the right people are finding us now, or the macro trends have shifted, but it's easier to get people excited about the open source component of our future. But still hard to tell if that's sample bias based on things that have changed in our world.

I get the sense that the slowing down of blockchain mania has helped.


Hey JJ!

  • What are the main things to consider re: licensing when one intends to start a commercial oss project?

  • Have you seen big licensing issues arise when a side project ends up becoming a commercial project?


How practical (or irrational) are fears of a budding startup going the open source route from having business logic stolen from competitors?


I am the founder of OpenDomain - we have donated domains worth millions to Open Source projects over the last 20 years. Domains including Drupal.com, OsCon.com, Xmpp.Org, Ecmascript.Org, FosDem.com, Schema.Org to Google, and WebPlatform.Org to the W3C. Unfortunately, we have not gotten a lot of love from OSS, so we are thinking about ending the project. We would love your opinion if we should continue. I am considering selling all my current domains (NoSql.Com, Free.TV, Xg.Org, 4NY.com, and more) to fund a new open source project: CharityCoin. CharityCoin is a 'Better bitcoin', where part of the mining goes towards charities. We won the techstart blockchain hackathon becuase we have a better PoW, but I am concerned about creating another altcoin because of the recent drop. Is there still room to create a new Coin? We also have a great idea on how to do an ICO without all the headaches.


Appreciate ya taking the time to do this, JJ! How would you define an open source company?


Hey Michael! I try to call them "COSS" companies as I think that puts a finer point on it. For COSS companies, I like to define them using the following working definition: "If a given company fundamentally relies/depends on a core OSS project (or a handful, like Hashicorp, for e.g.), to justify its own existence, it is therefore, definitionally, a COSS company". I have blogged a bit more about this here: medium.com/open-consensus/1-the-10...


Hi JJ, is there a "why now" reason for open source, or has major investment in commercial open source always been feasible?


Hey! thanks so much for doing this! Sounds like you are involved in a lot of different types of projects. Do you have any productivity tips?


Timing question.

When do you open source? Once you have team and funding that can build a business around the product or when you are still in single founder stage?

Classic DEV Post from May 26

How to Stay Fit Physically and Mentally and Keep Coding

Throughout the last year, I have worked part-time as a working student and also studied at the university. I was not the first and not the last one who has combined that during their studies, but the problem for me was, that at the end of the day I have felt absolutely exhausted mentally and physically. That caused problems with my health and motivation to continue working on my goals or anything. (yeah, “goals,” I wish I had something more specific at that time).

Joseph Jacks profile image
Self-taught coder, musician, writer, tech architect and all around curious person. Founder of Open Core Summit KubeCon, Kismatic, OSS Capital, Aljabr and a few other things. Investing in open things!

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