Jaisen Mathai

Giving In To Generosity

2026-03-04T00:00:00-08:00

The Bible has a lot to say about generosity. While it doesn’t only talk about money, that’s what I’m writing about today.

Secularly speaking, I’ve had a very healthy relationship with money. I live within my means and save diligently.

Biblically speaking, I’ve struggled. I tithe regularly and often give generously beyond that. But money has a way of pulling me toward security and status. Financial security, early retirement and proving to myself and others that I made it are all real ways that money takes my eyes off what really matters. Biblical generosity has nothing to do with the money and everything to do with honoring God. It’s a subtle but massively important distinction.

In my core, I know that I want unadulterated devotion in my faith. While I can be ruthless to myself, my faith lets me be equally gracious. This means I get to be fully honest and really explore my motives. Because, on the surface they are fine. Financial security can be masked as providing for my family.

Giving in to generosity means I need to systematize it. It needs to be on autopilot to avoid the risk of me mucking around with it. I’m still learning how to do this but here’s what I’ve come up with so far.

Donor Advised Funds

I initially looked into DAFs because of their tax efficiency. I do love that about them. But what I love more is that they let you take large steps of faith. We donated 5 years worth of charitable giving at the start of 2026 to our DAF. It was quite frightening because once I clicked that button, there was no way to claw the money back.

I contemplated doing it for weeks. But once I did it, I felt complete relief. All the fear I had vanished. I was surprised.

I was more surprised in the weeks after as my attitude towards the funds in our DAF shifted from we will spend this over 5 years to I think we can probably spend it all this year. Taking that first step and clicking the button flooded my heart with generosity. It’s a couple months later, and that hasn’t changed.

Charitable Business Ventures

I have a penchant for building things, trying to get others to use them, and trying to turn that into a business.

If it’s inevitable that I do that, why not try and weave generosity into it?

I’m experimenting with a business model where the operating costs are near zero and all of the profits go to charity. You can read more about how I think that can work on Lattice’s mission page.

This idea particularly interests me because it lets me pursue something that feels natural to me while orienting it towards generosity from the start.

Sometimes I think that in the grand scheme of things that all of this is silly. And in some ways, from the outside, it is. But when we lift our eyes to God, He begins work on the inside.

Giving In To Generosity was originally published by Jaisen Mathai at Jaisen Mathai on March 04, 2026.

My Ridiculously Robust Photo Management System (Immich Edition)

2026-01-16T00:00:00-08:00

TL;DR: Changes to albums, descriptions, location, date/time and favorites through Immich are stored in the photo’s EXIF and automatically backed up to my Synology NAS and into Dropbox; no database needed. Below is a video for those who prefer to watch instead of read.

I created a simpler version of the plugin I use that is suitable for those with their own workflows which might differ from mine. It’s available at immich-exif.

I’ve been working on my photo management and archiving workflow for over 2 decades. It’s changed a lot over that time but usually in bursts. It works really well and I don’t have to touch it much.

By far, the most durable aspect of my photo management workflow is that it only relies on EXIF to store metadata about photos. No reliance on an external database to keep track of descriptions, favorites or albums. I’m not sure of any other workflow which does this but I think they all should. But we’re not here to talk about that. I want to tell you all how I’m using Immich.

I outlined my philosophy for photo management in detail in another post but I’ll summarize them here in order of importance.

Preserve. My photo library needs to be future-proof for decades into the future.
Unify. Photos from my wife and my phones need to be combined into a single library.
Experience. The photos and videos need to come to life and help us re-experience the moments when they were taken.

I was using Google Photos as a read-only viewer of my photos and fell in love with the discovery features. But a change back in 2019 to how Google Photos and Google Drive worked together broke my workflow.

The primary source of my photos is my Synology NAS at home. I organize my photos using a simple command-line tool, named Elodie, that I wrote over 10 years ago that’s grown to 10k lines of code, 1,300 stars and 150 forks. The best way to describe it is that it materializes your photo library onto the file system using only the EXIF. It’s my canonical organizer.

I clobbered together a plugin for Elodie that would replace the Google Drive + Google Photos capabilities that Google deprecated. This let me continue using Google Photos as a read-only viewer for my photos. But I was growing tired of relying on Google services and especially handing over all of the data embedded in my photos. So I stopped using Google Photos.

I was left with several years of not having a great way to view my photos. I desire a richer experience than the folder-based default experience I have with Synology and Dropbox. I was very optimistic about Synology Photos but it was unfortunately underwhelming. Maybe because my Synolgoy NAS is 10 years old but I also didn’t want to upgrade it.

I’ve been hearing a lot of positive feedback from others about Immich and had been keeping a close eye on it. At the end of 2025, I decided to take a closer look. The aha moment was when I learned about external libraries. If you’re not familiar with them, they’re existing folders that you can tell Immich about and it’ll add them to your photo library. Most importantly, you can mount them as read-only.

I immediately drew paralells to my prior use of Google Photos. I quickly determined that I could restore what I lost with Google Photos using Immich. But I wondered … what if I could do more? Been wondering for a few years, actually.

I've been thinking, for years, about an easier interface to manage my photos using @getelodie (the Github version) than the command line. I haven't put my finger on it.

Probably doesn't have to work on mobile. Probably web. Mobile / desktop apps deteriorate quickly anyways.
— Jaisen (@jmathai) October 31, 2022

Turns out the answer is yes. I was able to turn Immich from a read-only viewer to a full fledged way to organize my photos while relying only on EXIF. Now, Immich doesn’t modify EXIF of photos. Instead, it stores information into its Postgres database. Immich can read from and write to XMP sidecar files. But sidecars are too clunky for me. I want everything embeded in the photo file itself. As far as I understand, Immich authors don’t want to edit the original photo file. I get their reasoning but I still want to be able to.

What I thought would require a 4 hour session with Claude Code turned into a two week rendevous learning a lot more than I anticipated about how Immich works. External libraries are great but there are some obvious gotchas with how Elodie works. If you add a photo to an album using Elodie then it will update the photo’s EXIF and also move the photo into a folder with the name of the album. To Immich, this is interpretted as deleting the original file and creating a new one. This creates all sorts of challenges but I was able to solve it using an eventually consistent approach. This means, all of the changes are stored and will eventually materialize.

There were other smaller challenges but I was able to overcome them all with some elbow grease. Immich’s API is pretty great and I’m probably just scratching the surface. But for now, I’ve been spending a lot of time enjoying my photos like I haven’t been able to for a while without compromising my core principles for making sure they’re around in a couple decades.

A detailed technical explanation is outside the scope of this post but if folks want to know I’ll write it up separately. For now, follow GitHub issue 496 to track progress and see the code.

My Ridiculously Robust Photo Management System (Immich Edition) was originally published by Jaisen Mathai at Jaisen Mathai on January 16, 2026.

Latent Product Development

2025-01-05T00:00:00-08:00

The best products and features emerge naturally from within your subconscious.

la·tent: lying dormant or hidden until circumstances are suitable for development or manifestation.

There’s something special about a good product. They’re malleable and composable within its intended use while holding onto some opinions. This doesn’t mean that they are full of features. In fact, it’s often the opposite. Many have few features which tend to be quite simple. A great product doesn’t have to do many things. It just needs to do all of the things it does exceptionally well.

What happens when you let ideas simmer in your subconscious? Their rough edges start getting slowly sanded away one by one. But something more important happens. You arrive at an inflection point where it feels right in ways the original version of your idea didn’t. Sometimes it’s a single breakthrough idea and other times it’s the culmination of many smaller ideas. This is the point where you really fall in love with it. Fielding questions you’ve never considered before will feel natural and your confidence talking about it will increase.

I get pitched a lot of ideas and I almost always encourage people to think deeper about them. Not in a forced way though - that does not yield novel results. Then how, I wondered. This is what’s worked well for me.

Take breaks often while working before your brain feels overloaded.
Perform activities which require low mental attention like walking or showering.
Start your morning with something relaxing like sitting on a couch drinking coffee (no devices).
End some evenings early and to go lay down in bed before you're tired.

The common thread is that latent thinking will happen naturally when your brain is in a restful state for 15 minutes to 30 minutes. Not much to ask in exchange for great ideas.

Latent product development is easier to do on smaller teams where everyone pays attention to craftsmanship. You can tell if the craftsmanship is ingrained into every aspect of the product including what the user does and does not see. I’d say it’s part of the team’s culture.

If your product has a well defined 24 month roadmap, forget it. There’s no room for latent product development. The entire product is extruded through the machine. The incentives are aligned elsewhere for reasons that are important for some.

Latent Product Development was originally published by Jaisen Mathai at Jaisen Mathai on January 05, 2025.

Life of a Blockchain Transaction - (Proof of Work)

2021-10-29T00:00:00-07:00

This article is also available as a thread on Twitter.

The life of a crypto/blockchain transaction. Proof of Work version. #web3

// THREAD //

👇🏾
— Jaisen Mathai (@jmathai) October 29, 2021

The life of a crypto/blockchain transaction. Proof of Work version.

You use your favorite app to purchase 1 ETH. The app creates a transaction and broadcasts it to the network. The transaction includes metadata including transaction and gas fees that you are offering to someone (aka a miner) for adding your transaction to the blockchain.
Your transaction enters a pool of unvalidated transactions waiting to be added to the blockchain by a miner. The likelihood of your transaction being selected by a miner is based on the amount of fees you are offering. Most apps will determine this fee on your behalf.
Many miners compete to add the next block to the blockchain. A block can contain any number of transactions greater than zero as long as it fits within a certain size. The winning miner is rewarded some of the cryptocurrency as well as all the transaction and gas fees.
Adding a block to the blockchain requires miners to find a hash. The hash is based on the data within the transactions AND the hash from the previous block. This is what makes it a chain because each block’s hash includes the hash from the prior block.
A hashing algorithm takes input data and gives back a string of characters. The SHA256 algorithm used by Ethereum generates a 64 character hash - making it practically impossible for any two input data to have the same hash.
The hash must meet certain criteria before it can be validated. It must be correct AND be lower than the “target hash” set by the network. For example, the hash “zzz” is HIGHER than “000”. Think of it as a sorted column in a spreadsheet.
It’s rare that the hash of the transaction data plus the prior block’s hash will be lower than the target hash. In order to generate a valid hash, miners will add a number (aka nonce) as part of the input data in hopes that it’s lower than the target hash.
The network dynamically sets the target hash to varying levels of difficulty based on the number of miners. The more difficult a target hash, the less profitable it is to be a miner & vice versa. This regulates the # of miners and adds a level of consistency to the network.
Miners end up trying LOTS of nonces before finding one that generates a valid hash. The energy required to do this is what is referred to as the “work”. The faster a miner can generate hashes (aka hash rate), the more likely they win the chance to add the next block.
When a miner generates a hash they believe to be valid, they send the hash, nonce and transactions to be validated by a node on the network. Validators can quickly determine if the proposed block meets all of the criteria before adding it to the blockchain.
This process starts all over each time a new block is added to the blockchain. Miners have to repick unvalidated transactions and start generating hashes. Your transaction is confirmed once it is included in a block that is added to the blockchain.

I’ve read a lot of documentation and articles which helped me understand how blockchain transactions work. Read the articles below or contact me if you have questions.

Life of a Blockchain Transaction - (Proof of Work) was originally published by Jaisen Mathai at Jaisen Mathai on October 29, 2021.

Startup Acquisition Video Log

2014-09-15T00:00:00-07:00

2014-01-21 (January 21st, 2014)

My initial video documenting the last 5 months before Trovebox was acquired. At this point my primary focus was on sales. I was cold calling customers and trying to close a sales deal with Columbia Law University.

2014-02-12 (February 12th, 2014)

We arranged to have booths at 3 conferences. Columbia Law University got back with us that our proposal was too high. We were also working with University of Southern California to partner on a solution to have digital yearbooks in schools.

2014-02-13 (February 13th, 2014)

We were hitting some pretty large headwinds with proposals not landing well with regard to pricing. Our other discussions were dragging on too. Overall the long sales cycle were not looking favorable given our runway.

2014-03-05 (March 5th, 2014)

My co-founder and I decided to shut Trovebox down. This decision kicked off several secondary initiatives. The first was to shut the service down while living up to the promise of data portability. The second was identifying a plan B to identify possible acquisitions.

2014-03-09 (March 9th, 2014)

We started talking to our mentors about what to expect when shutting down and what our options were. We wanted to make sure and deliver on our promise to users of data portability and felt confident we could do that.

2014-03-18 (March 18th, 2014)

We had our first of many meetings with companies interested in an acquisition. This meeting was with 10 people at Western Digital including Directors, VPs and SVPs.

2014-03-24 (March 24th, 2014)

This starts the cat and mouse game of waiting for a response from Western Digital. We presented to them 6 days prior. The attendance grew from 10 to 15 people to whom we demoed and answered questions.

2014-03-27 (March 27th, 2014)

We didn’t hear back from Western Digital yet so I sent a follow up email. They responded that they would like to set up a follow up meeting. In the meantime, I started coding a little bit to deal with the stress.

2014-03-29 (March 29th, 2014)

We met with a Director at Dreamhost to discuss interest in an acquisition.

2014-04-23 (April 23rd, 2014)

We had an idea that I decided to file a provisional patent for before presenting the idea to Western Digital. The idea was to have Trovebox running on NAS devices and with the ability to communicate with other NAS devices. This would create a network of tens or hundreds of thousands of NAS devices which had the ability to communicate with each other. I demoed a working prototype of this on their MyCloud NAS devices.

2014-04-29 (April 29th, 2014)

The idea of running Trovebox on NAS devices continued to take shape. We essentially took all the technology we created and quickly pivoted to an entirely different product. I installed Trovebox on several additional NAS devices and shipped them to family in Ohio and New York. We started showing the prototype to others with favorable feedback.

2014-05-06 (May 6th, 2014)

More cat and mouse with Western Digital. New opportunities started to arise with NetGear and IdeaLabs. We considered pivoting to this new idea but ultimately decided not to pursue the idea and continue focusing on acquisition opportunities.

2014-05-12 (May 12th, 2014)

Demoed the prototype running on a NetGear ReadyNAS to an SVP at NetGear. Discussions with Western Digital were progressing slowly but showed signs of hope.

2014-05-14 (May 14th, 2014)

Western Digital asked us to come back and demo to an EVP who would be the final decision maker. NetGear wanted a follow up meeting as well.

2014-05-16 (May 16th, 2014)

Demoed the prototype to an EVP at Western Digital.

2014-05-19 (May 19th, 2014)

Demo with Western Digital went well. I ran into some technical difficulties preparing the demo but was able to improvise. Discussions moved forward with Western Digital and we ultimately sold the company to them. I spent the next 2 years integrating our software onto their NAS. We successfully completed this and had our apps approved in the Apple App Store and uploaded to the Google Play Store. In the final stretch, new leadership that recently joined decided to kill the product before launching. I left the company several months later.

Our idea of an interconnected network of 10s of thousands of NAS devices that could safely store your photos while securely accessing your friends’ photos without the need of a centralized service never went beyond a prototype or outside the walls of Western Digital. Many of the ideas are resurfacing 5 years later as part of Web3.

Startup Acquisition Video Log was originally published by Jaisen Mathai at Jaisen Mathai on September 15, 2014.

My Shuttleworth Fellowship

2014-09-11T00:00:00-07:00

We are the Shuttleworth Foundation and we fund people who are unafraid to re-imagine the world and the way we live in it.

There exists in Cape Town, South Africa a small group of people taking bold risks by investing in people ambitious enough to change the world through openness. I only came to know about the Shuttleworth Foundation in 2012 while we were looking for funding sources. It’s founded and funded by entrepreneur Mark Shuttleworth .

On the surface the Foundation looks like part venture capitalist and part foundational grant institution. It’s an accurate description but to say that’s all the Foundation is would be a gross understatement.

Bi-annually the Foundation gives up to 3 years of fellowship to individuals working on something in an open manner . That includes openness in education, science, data, government, software and more. The Foundation measures success not in dollars but in positive social change.

My fellowship for Trovebox

My fellowship was for Trovebox (originally OpenPhoto). We set out to make possible the preservation of digital photo archives for posterity. Openness is innate to solving that problem. Ideas like data ownership and portability need to be cornerstones; not an afterthought. Our approach of open sourcing our software and experimenting with distributed storage for digital media are what made it a good fit to receive a fellowship.

We experimented with and prototyped having Trovebox installed on a NAS. Credit: Jaisen Mathai CC BY.

A mix of funding and community

The Foundation provides over $1,000,000 in funding over 3 years. It takes a lot of resources to do big things and the financial support provided by the Foundation is critical. But it’s the less interesting of two components.

I came for the money and stayed for the community. – Me

It’s impossible to know how the community plays into a fellowship until you arrive at your first Gathering. The Foundation has bi-annual Gatherings where every fellow, current and alumni, converge in a single location. It’s a week crammed together in a room talking about everyone’s projects or around a dinner table discussing everything from the lack of transparency at large corporations to putting educational materials into the hands of the poor in South Africa .

At a Gathering in Edinburgh, Scotland. Credit: Jason Hudson CC BY.

I’ve been surrounded by brilliance at many points in my life but I’ve never been inspired like I am when I’m with this group of people. The support system between fellows was unparalleled.

Experimenting is in the DNA

Each fellowship is unique despite sharing a common thread of openness. The Foundation understands that to get from point A to point B you might have to go through point C. And some of those times you end up at point Z which was more interesting than point B in the first place. I appreciated that they were always supportive of experimenting and changing course as a result.

I recall my fellowship and some of the changes we made which led me to feel we weren’t making any progress. The Foundation remained patient and supportive as I eventually found my way back to where I started. But this time I arrived equipped with a war chest of knowledge and a completely new and novel approach.

It took us 3 years but it had to take us three years. - Me

Most amazingly I remember talking to Helen and Karien in Budapest at the Gathering in May of 2014 about my contemplation of not applying for a third fellowship. I was excited about what we learned and the new approach we had at making permanence of media archives possible. At the same time I was exhausted and couldn’t see the path to sustainability. I’ll never forget Helen’s response urging me to apply again. That’s not the type of commitment or support you come across often.

Ultimately I decided not to apply; one of the most difficult decisions during this journey.

Becoming an alumni

By now I’ve been an alumni for just over a week. The Foundation published Arthur and my exit from the fellowship program on their site today. Reading that page and watching the video made the transition from my fellowship to the next chapter quite concrete.

It’s hard to put into words how much my fellowship meant to me and how much I learned as a result. As I continue towards our original goal of permanence for digital media I’ll do it with more openness, more ambition and with the support of a small army of people around the world.

Once a fellow, always a fellow.

My Shuttleworth Fellowship was originally published by Jaisen Mathai at Jaisen Mathai on September 11, 2014.

Timeline

2014-09-10T00:00:00-07:00

Over the 3 years we spent building Trovebox there were countless successes and failures. All of which helped shape the company, product and founders.

Below is a timeline view of events that makes it possible to quickly consume most of the ups and downs we had.

May 2011 - December 2011 (before funding)

The first months were some of the most exciting. We built a product from scratch and gained a following.

May - I left my job to start OpenPhoto. The first milestone was a successful Kickstarter campaign .
Aug - OpenPhoto was accepted into Mozilla WebFWD
Sep - OpenPhoto was a standby for TechCrunch Disrupt. We didn’t get to participate in the contest but were offered the chance to have a table in Startup Alley.
Sep - Pitched to Kapoor Foundation by way of intro from Marco DeMiroz. Did not get past first meeting.
Oct - Version 1.2 of OpenPhoto was released (7 contributors).
Oct - Initial beta version of iPhone app via TestFlight.
Oct - Pitched to Khosla Ventures. I met Vinod Khosla at TC Disrupt who asked that I contact him afterwards. Did not get past first meeting.
Nov - Version 1.3 of OpenPhoto was released (4 contributors).

January 2012 - July 2012 (before funding)

The first half of 2012 was largly focused on securing funding.

Feb - Was invited to interview with IO Ventures. This is a selective process and they receive 700 applications of which 40 get asked to interview. We did not get accepted.
Feb - Was invited to pitch to Band of Angels. This is a selective process and we were 3 of 50 companies selected to pitch. Did not get past the pitch.
Apr - OpenPhoto iPhone app released in the App Store.
May - Released “Import from Flickr”.
Jun - Released “Import from PicPlz”. This was our first initiative at providing an option for users of sites that were shutting down or making terms of use changes.
Jul - Version 3.0 of OpenPhoto was released (18 contributors).

August 2012 - December 2012 (after funding)

After receiving funding we got back to focusing on the product.

Aug - Received Shuttleworth Foundation fellowship.
Nov - Added support for 5 cloud storage providers.
Dec - OpenPhoto Android app released in the Google Play store.

2013 (after funding)

As we entered 2013 we focused almost entirely on sales and marketing to fuel growth. We decided in May to pivot to targeting businesses.

Jan - OpenPhoto relaunched as Trovebox (6 contributors).
Apr - Archive.org support added.
May - iPad support added to iOS app.
May - Realized that growth with consumers was too low and that we needed to find an alternative.
May - Partnered with Insight Sales Dynamics (ISD) and worked with Brian to land large enterprise deals.
May - (ISD) Meeting with CEO from Topia Software. Had 3 calls but did not close.
Jun - (ISD) Meeting with VP at Sony. Met in person 4 times over 8 months but did not close.
Jul - Group support added to Trovebox.
Jul - Received 2nd year Shuttleworth Foundation fellowship.
Sep - (ISD) Meeting with VP at Roku. Had 2 calls but did not close.
Oct - Switched Trovebox from consumers to businesses.
Dec - Released Trovebox Collect.

2014 (after funding)

This was an important year for us as we focused on growing our customer base by targeting businesses. We tried everything from cold calling companies to exhibiting at trade shows.

Jan - Began cold calling group travel vacation companies. This lasted a month and the results were terrible.
Feb - Launched beta of video support.
Mar - Exhibited at 3 expos. This was sort of a last ditch effort to try and figure out a strategy or market which would provide significant growth for us with businesses. This wound up not working out and we decided that we couldn’t get the growth we needed.
Mar - Considered Kickstarting a TroveboxHome project which would be a physical network attached storage device that ran Trovebox software or otherwise communicated intelligently with Trovebox in the cloud. After speaking with Dr. Song we decided not to pursue this idea.
Mar - Reached out to prior ISD contacts about opportunities and Western Digital was interested. This resulted in a meeting with about 15 key people from Western Digital’s Branded Products group.
Mar - Met with Western Digital and demoed our product. We had met with them a year earlier to private label our software but nothing materialized.
Mar - Met with Dreamhost to discuss interest in an acquisition.
Apr - Prototyped Trovebox running on a Western Digital MyCloud device. Demo’ed to Western Digital.
May - Prototyped Trovebox running on a Netgear ReadyNAS device. Demo’ed to Netgear.
May - Demo’ed to Drobo.
Jun - Signed Letter of Intent from Western Digital to be acquired.
Jul - Joined Western Digital.

Timeline was originally published by Jaisen Mathai at Jaisen Mathai on September 10, 2014.

The Struggle

2014-08-07T00:00:00-07:00

There were many days and even weeks where I was convinced all this was a huge mistake. Ben Horrowitz, a well known venture capitalist, blogged on this topic in 2012 in blog post also called The Struggle .

It’s complicated

Us humans are neither binary or entirely logical; thank goodness. We’re complex creatures and what constitutes happiness, contentment, joy or any of the opposite emotions depend on a large number of factors. This makes The Struggle even more acute.

It started for me near the end of 2011 when we were failing to raise funding. I knew we absolutely needed to secure funding to succeed. I won’t go into the details of our fundraising journey in this article but you can read about it here.

Being a team

The pros of having a co-founder undoubtably outweigh the cons. But I’d be lying if I didn’t admit that having a co-founder increased the pressure I put on myself. If we couldn’t figure out how to make Trovebox successful then I’d feel some guilt along with it.

Santa Cruz with Patrick during his first visit. Credit: Jaisen Mathai CC BY.

Understanding my motivations

There was a clear consequence of not getting investment; we’d have to abandon and shut down OpenPhoto. Founders start companies for various reasons but there’s always a common thread of believing strongly in something. It might be a belief that building something will improve people’s lives, make you a lot of money or change something that’s in need of change. Most often it’s a combination of these that drive founders.

I believed OpenPhoto needed to exist. I’m a bit of a nostalgic. I love to relive past moments. Furthermore it became really important to me that we preserve the memories of our family’s everyday life. One day I hope to sit with my kids and show them photos of their childhood; much like my own parents did with me.

I believed something needed to be changed. Looking around at how everyone dealt with, or didn’t deal with, archiving photos I knew something had to change.

I believed we could build a successful busines. I’ve always been driven to create businesses. In middle school I would buy Zotz candy for $.03 and sell it for $.05. A hefty 66% margin.

As with any strong belief it’s difficult to come to terms with the idea that things won’t pan out the way you believed.

But there’s a tougher reality that had dawned on me.

Does shutting down mean failure? How would I explain this to friends and family who thought I was making a mistake when I left Yahoo? Do I just go back and get a normal job?

Hello ego, pride and insecurity. Not traits I’m particularly proud of but they helped motivate me to continue building OpenPhoto. I imagine ego drives more entrepreneurs than you’d think.

The effect of having no money

Louis C.K., a comedian, has a great bit titled Being Broke . Besides being hilarious I felt like I could relate¹.

You ever have negative money? You look at your bank account and you have negative $10. […] I wish I didn’t have anything but I have less than that. If it’s free I can’t f*****g afford it.

It turns out that the lack of money can act as a crucial forcing function. When you’re facing the reality of shutting down a startup because you can’t pay your bills you’ll quickly focus on what matters most. Even in hindsight I know we didn’t waste much time focusing on the wrong things. I have our dwindling bank account to thank for this.

Growth is everything

There was one thing that rang true on each day of Trovebox: growth. Growth shares many characteristics with fundraising. Namely growth is largely out of your control and all you can do is try and make the stars align.

The feeling of not acheiving growth was as stressful as when we couldn’t finding funding. It was a sign that the product was headed in the wrong direction and it felt like we were trying to turn the Titanic around.

I spent the beginning of 2014 going through a spreadsheet of 600 potential customers we could sell to. I called them up on the phone and in the unlikely event there was interest it started a series of calls to close a sale. None of them panned out.

Perhaps our product wasn’t solving a need as critical as our earlier conversations with customers implied. Maybe it was that we grossly underestimated the length of the sales cycle.

I don’t believe we’ll ever know.

Dashed hopes

Then you have the golden opportunities. Ones which have all the signs and promise of being a home run. We had promising meetings with execs from Sony, Netgear, Roku and Western Digital. We even met with Sony 4 times in San Diego. Nothing.

Smoking cigars with our sales lead to celebrate one of our meetings. Credit: Jaisen Mathai CC BY.

These were particularly difficult because when we crashed we crashed hard. Forging partnerships with companies is difficult because you have little insight into their roadmap. A company maybe highly interested but then go silent for 6 months and come back to restart the conversation. You can only do your best and stay on their radar.

Everyday will bring a struggle

Those are some of the larger struggles I remember. But every day brings struggles. A lot of it is psychological and emotional. Keeping on top of that without losing your sanity isn’t easy.

That’s why it’s so critical to have a good support system. Else you’ll got nuts and take your company down with you.

¹ Just a disclaimer that I’m not implying I was poor. When I think of people being poor it’s not just a lack of money but a lack of opportunity. I empathize greatly with people who find themselves in that situation. I never considered myself poor despite not having money.

The Struggle was originally published by Jaisen Mathai at Jaisen Mathai on August 07, 2014.

My Support System

2014-06-05T00:00:00-07:00

It was over 3 years ago when this journey started. I thought if things went terribly that it would last as little as 6 months and if things went really well it could have gone on for a decade.

Curveballs.

It’s the part that makes startups hard: managing your own psychology when it looks like everything is falling apart.

So many times it felt like everything was falling in around us. I can recall the 3 times Patrick and I talked about how there’s no light at the end of the tunnel. Twice on Castro St. in Mountain View where we worked when Patrick was in town we planned how we’d shut Trovebox down.

When they say your chances of success increase if you have a great co-founder this is what they must have been talking about. On my worst days it felt like Patrick was the only one who could pull me out of the depths. Those days were plentiful.

Family

Despite the consuming nature of doing a startup my first commitment was always to Rachel and our 2 kids. Rachel didn’t know what she was signing up for on that day when I asked her what she thought about me leaving my job and decent health insurance along with it. Life threw us many curveballs but I had her unflinching support at every turn.

Mi familia. Credit: Jaisen Mathai CC BY.

Then there’s my parents who think I’m crazy. That gets reinforced each time I chase a startup idea. This is the second time I left a job to start something. They want nothing more than for me to get a job at a big stable company and be a loyal employee until I retire. Nonetheless they supported me as they have in the past despite thinking I was being foolish.

The Shuttleworth Foundation

I wrote in more detail about my experience as a Shuttleworth fellow if you wanted to read it. But to make a long post short they’ve been the best partner I could ask for. Not only did they provide nearly $1M in funding but they provided a network of the brightest and most ambitious people I’ve met. All working on something that makes the world a better place. There’s nothing else quite like it.

Shuttleworth Gathering at the MIT Media Lab. Credit: Jaisen Mathai CC BY.

Friends

There were countless friends who believed in me as well. They helped me keep my sanity when I questioned if I had made a terrible mistake.

It doesn’t take a village to build a startup but it helps to have people in your corner. You don’t need them every day but you will need them.

My Support System was originally published by Jaisen Mathai at Jaisen Mathai on June 05, 2014.

Pivoting

2013-05-02T00:00:00-07:00

Startups don’t come with maps; there’s no clear path from idea to a successful product.

We launched OpenPhoto with the hopes of helping regular folks like you or me better organize, archive and share photos. Our approach was different; we wanted to do so in a way that could guarantee your photo library would outlive our company.

We enjoyed success that most startups never do. We did a successful Kickstarter , had people all around the world installing our open source software , signed up tens of thousands of users at Trovebox and raised funding.

Still we didn’t do enough to build a sustainable business by offering our service to consumers. I wrote in more detail about our transition away from consumers on Medium .

The Decision

Our internal dashboard highlighted a single graph: revenue growth. I knew we needed weekly growth to reach sustainability in a reasonable time. We couldn’t simply add a few accounts each day we needed the signups to compound. Our target line on the graph grew exponentially but our actual line was growing linearly. This was bad, very bad.

Around this time we noticed there were more and more businesses using Trovebox. Naturally we decided to find out exactly how these companies were using it. After numerous conversations we felt there was a tremendous opportunity in an underserved market.

The consumer photo space is crowded. You’ll be hard pressed to find another market with more products and startups competing for consumer eyeballs. Businesses, however, don’t have many options that suit their needs. Consumer services don’t support multi-user accounts and don’t offer ways to easily source photos from teammates.

The Plunge

It took us a few months to make the transition but we finally relaunched Trovebox as a business product in November. Coincidentally a competitor released business metrics outlining their struggles building a subscription based consumer photo service. It was further validation that we had made the right decision 6 months earlier.

We immediately focused on growing our business customer base. We had similar internal charts on our dashboard along with a 6 month target growth line we needed to track.

Despite cold calling, working with sales people and exhibiting at expos we were struggling and the graphs weren’t looking good. It was around this time that I had a conversation with a friend which led to the idea of selling network attached storage with Trovebox installed and configured on them.

360 Degrees

The idea of network attached storage devices running our Trovebox software had legs. As I described it to people they loved it and if I had the chance to demo it their eyes lit up. Much moreso than when I described Trovebox as a cloud hosted photo service.

We experimented with and prototyped having Trovebox installed on a NAS. Credit: Jaisen Mathai CC BY.

Remember when I said there’s no map? If there was a map I would have found a more direct path to this product. Instead it took us 3 years to get here which was the only way to arrive.

Pivoting was originally published by Jaisen Mathai at Jaisen Mathai on May 02, 2013.

Road To Funding

2012-08-01T00:00:00-07:00

Runway is what start-up founders call the amount of time until there’s no money left to feed their kids. Prior to funding, a start-up’s runway is a function of each founder’s ability to survive without collecting a paycheck. Since Rachel was staying at home with Tavin (and later our daughter Elodie) it meant our runway was whatever money we had available in the bank and brokerage accounts.

Kickstarting OpenPhoto

It was 2011 and Kickstarter was only 2 years old. The largest campaign hadn’t yet broke the $1M funding level. It was also a time when Kickstarter had to approve which projects could launch a crowdfunding campaign on their site. Fortunately they picked an idea I submitted.

I launched my Kickstarter campaign for OpenPhoto on July 1^st of 2011. It was an intense 30 days during which I received press coverage from Techcrunch , ReadWrite and others. By the end of the campaign I crossed my funding goal by raising $25,242 of my $25,000 goal. The successful funding from Kickstarter helped validate not only that people were interested in OpenPhoto but that they were willing to pay for it.

The Kickstarter funding wasn’t a proper angel or seed round but I knew it would help. In fact, the exposure from Kickstarter helped get us accepted by Mozilla into their WebFWD accelerator . WebFWD didn’t include any funding but legitimized us a little bit more and we got access to some great mentors and investors.

It was time to turn that into a successful angel round.

When our start-up met reality

Determined to close a round of funding by the end of 2012 I warmed up leads and had a spreadsheet of a couple dozen angel investors I knew by 1 or 2 degrees of separation. I probably still have that spreadsheet laying around; it’d be fun to dig up.

It would be 9 months longer than the 6 months I told Rachel before we’d get funding. That’s 15 months of not getting a paycheck. Founders tend to underestimate the time required to raise funding. Knowing that, I felt 6 months was both aggressive and realistic.

Let me fill in what happened during those those 15 months.

The first wave

Between October and March we talked with numerous angel investors while also pitching Kapoor Ventures and Khosla Ventures amoung others. I knew the pitches weren’t going well. If an investor is interested, you’ll know. I knew anything else meant there wasn’t chemistry.

“I have reviewed the idea and the material with [partner] and our team, and we’ve decided it’s not a fit for [firm].” – one of the VC firms we pitched

When fundraising it’s vital not to take rejection personally or as a sign you won’t get funding elsewhere. This is one of the most difficult parts of fundraising. I had prepared for maximum rejection and it was paying off; the rejection didn’t phase me.

2012 came to an end and I was faced with a decision and an unfulfilled promise I made to Rachel. I experienced something at that time which would be a recurring theme over the next 3 years; Rachel’s unflinching support.

In February of 2012 we were invited to interview for the IO Ventures accelerator. Over 650 companies apply and they pick a few dozen to interview. I was optimistic about our chances but in March we got the email that we didn’t make it in.

Unfortunately I have to inform you that your company wasn’t chosen to participate in the spring i/o startup program. You were one of over 650+ companies to apply and made it to the last round in our process.

The thing about start-ups is you can only dwell on failure long enough to learn something and then you move on. There’s always too much to do in too little time. We continued looking at funding opportunities which led us to the Knight News Challenge.

I was introduced to someone at the Knight Foundation by the person we pitched to at Kapoor Ventures. I was too naive at the time to know better than to ask an investor who didn’t invest for an introduction to someone else. Nonetheless we wound up not receiving any funding from the Knight Foundation. As with previous dissapointments we didn’t let this stop us.

A most memorable pitch

Oh, this is good. My most memorable pitch by far was to the Band of Angels. We were one of 3 companies selected to pitch to a group of angel investors. Keep in mind that I’d been practicing this pitch for months. It had evolved but I knew the pitch like the back of my hand.

I arrived to pitch and was asked to wait in the lobby because a few of the angel investors were running late. My point of contact, Nicola, kindly showed me to the room in which I’d be pitching. I was expecting the room to be empty and for the investors to arrive shortly after me. Turns out all the investors were packed into this room and I was sat down in a chair. The formalities were skipped and before I knew it I was fielding questions about how our Dropbox integration worked and what our projected revenue was. I knew all of this but the shock precluded me from articulating it.

The entire thing was a blur. Once in the parking lot I called Rachel who was waiting to hear how it went. I was devastated. The next 20 minutes was spent in my car with me wondering what the hell just happened. You just don’t get many opportunities like this and I absolutely blew it.

Unsurprisingly, I received an email from Nicola in March letting me know we weren’t selected to pitch to an even larger group of investors.

We know that this process can be somewhat intimidating.

No shit.

Reflecting on failed funding attempts

By now we had spent more than 6 months trying to raise funding. It was starting to seem hopeless. Fundraising is a complicated beast. There are a few ways you can almost certainly secure funding. Traction and a prior exit; preferably the former. We didn’t have either.

This was a tough time as Patrick and I both faced the possibility of shutting OpenPhoto down. We took a long stroll down Castro street in Downtown Mountain View. We reflected on all the amazing accomplishments we made that year. No matter how well the community was going or how much a small group of afficiandos loved what we were building we simply couldn’t continue doing it without raising funding. That was the nature of our business and we were faced with it’s frailty.

We never decide anything that day.

The Shuttleworth Foundation

At any given point we were in discussions with or waiting to hear back from several potential investors. In February I had come across a foundation I’d never heard of before, the Shuttleworth Foundation .

The Shuttleworth Foundation invests in people working in the areas of open data, open science, open government and other open things. It was a long shot but that hadn’t stopped me in the past so I did the work to find out more about the foundation and figured out who I might know working there.

A friend of an acquaintence, Philipp Schmidt , had previously received a grant from the Shuttleworth Foundation. I talked with him and told him about OpenPhoto. He thought it was a good fit and introduced me to Karien Bezuidenhout , COO at the Shuttleworth Foundation.

I’d go on to receive a fellowship grant from the Shuttleworth Foundation. It wasn’t until later that I realized how fundamental the foundation’s fellowship model would be to the ultimate success of OpenPhoto.

It took roughly 14 months after quitting my job to get funding. That’s more than twice my promise of 6 months to Rachel; only days before our credit card bill was due that we couldn’t pay off.

The waiting was difficult but finding a partner in the Shuttleworth Foundation made the waiting worthwhile.

Shuttleworth Gathering at the MIT Media Lab. Credit: Jaisen Mathai CC BY.

Had Patrick and I been on the same continent we would have popped open a bottle of champagne.

Road To Funding was originally published by Jaisen Mathai at Jaisen Mathai on August 01, 2012.

My Best Day

2012-07-31T00:00:00-07:00

In order to grasp my elatement when I got off a Skype call with Helen and Karien you need to first read about our road to fundraising.

It was just a week prior when I got an email from Karien that I wouldn’t receive a fellowship from the Shuttleworth Foundation.

With a limited number of spots available, unfortunately we will not be offering you a Fellowship this round.

I was more than disappointed; the Shuttleworth Foundation was our hail mary. By this point I was running out of money and options. It had been over a year since I received a paycheck. Patrick and I still believed in OpenPhoto but we had failed to find a way to bring it to fruition.

That weekend I went to Austin, TX for my cousin’s bachelor party. One of the worst parts of doing a start-up is when others ask how it’s going and you’re having a particularly bad day.

I returned home from the bachelor party on Sunday and received an email from Karien on Monday, July 31.

Hi Jaisen,

Upon reflection we would like to have another conversation about a possible fellowship.

Talk about a roller coaster. I quickly replied that I could chat on Tuesday.

It was a 20 minute call with Helen and Karien that changed everything. For the first time in 15 months I was looking at a personal credit card bill that was larger than the balance of our bank account. Rachel and I were literally out of money after surviving off our savings and liquidating everything except our retirement accounts. And just like that we saw a flicker at the end of the tunnel.

We had received funding. Nothing else mattered.

I called Patrick immediately after getting this news and we were speachless.

What followed were 2 years of being a Shuttleworth fellow and finishing what we started in June, 2011.

My Best Day was originally published by Jaisen Mathai at Jaisen Mathai on July 31, 2012.

My Worst Day

2012-03-02T00:00:00-08:00

It was around 4pm on a Friday and I found myself stuck in traffic on 101 northbound. I was by myself so I couldn’t use the HOV lanes; not that they were any faster.

Typical scene on 101NB. Credit: Ed Hunsinger CC BY.

Let’s rewind a bit. Patrick first emailed me on June 30^th of 2011.

I’m offering my help because I think your idea is great and it will be something special. – Patrick, in his first email to me

I doubt he thought that email would result in him leaving his job and flying to the US just 9 months later. It was his first of many visits after he joined me as co-founder. Patrick was living in Belgium during the first two years of OpenPhoto. His visits became frequent and my kids adored him.

Deep thoughts in traffic

Back to that traffic I was stuck in. March of 2012 was a particularly difficult time for our company. We were making great progress on our product and signing up more users every day but we were struggling to raise capital. We didn’t realize this when booking flights for Patrick to come out to California.

There were a lot of thoughts running through my head as I stared at cars with people who had normal jobs. People I imagined at the time to not have the type of financial and business stress I was feeling that day. I thought to myself, “Patrick used to be one of those people.”

I wondered if I had ruined Patrick’s life. I also knew that I needed to greet him with a smile and enthusiasm at SFO.

It’s one thing to have a bad day because I’m stressed about my own life. There was something extra terrible to think about how my actions might have inadvertantly affected someone else’s.

A great first visit

The stress subsided once I arrived at his terminal and picked him up. Being in the same room and working together was theraputic for us and we accomplished a ton in just one week. It helped to get on the same page and come up with a plan we both believed in moving forward.

Don’t get me wrong. We had a lot of difficult conversations surrounding the business. But by the time he left a week later we felt confident in a plan to keep going.

OpenPhoto and Trovebox nearly died that week and I have Patrick to thank for its survival.

My Worst Day was originally published by Jaisen Mathai at Jaisen Mathai on March 02, 2012.

In The Beginning

2011-07-01T00:00:00-07:00

It was February 6, 2011 when I posted to HackerNews about an idea I had. The idea was a way store and share your photos while ensuring their permanence for decades into the future. This wasn’t the first idea I’ve had nor was it the first idea I’d end up leaving my job to pursue. In fact, this ended up being the third photo service I’d launch.

8 years prior I had started working on something named Photagious. It was 2003 and the Internet looked much different then than it does today.

Facebook or Flickr hadn’t been launched and everyone had a Hotmail account. Digital cameras were only starting to become popular and Kodak was still producing cameras and film. 5 years after starting Photagious we shut it down at the end of 2007. The hardest part of shutting the service down was receiving emails a year later inquiring if we had backups of the photos we had deleted prior to sending servers back to HP.

That’s when the seeds for OpenPhoto were planted though they lay dormant for several years.

Detoxing from start-up life in California

I was newly married and we had just moved to the San Francisco Bay Area from Ohio to start my new job at Yahoo!. The last thing I wanted to think about was pursuing another idea. Instead Rachel and I spent the next 3 years discovering and falling in love with Sunnyvale; the city we moved to.

My first day at Yahoo!. November 20, 2007. Credit: Jaisen Mathai CC BY.

In June of 2010 we had our son, Tavin. Life became infinitely better and busier. My collection of photos started getting infinitely bigger as well. We were taking a ridiculous number of photos and videos. They were all priceless and grew in value as Tavin became older.

I revisted the question of what to do with all these photos. It was important to us that they be around when Tavin was in his 20s and beyond. I began realizing that technology was converging to enable the organization and sharing of photos without sacrificing data ownership or portability.

The seeds for OpenPhoto had been planted.

Leaving Yahoo!

I decided to take the bold step of quitting my job to start OpenPhoto. With Yahoo! owning Flickr I didn’t want there to be any muddy waters. It wasn’t an easy decision but one I don’t regret looking back.

My last day at Yahoo!. May 31, 2011. Credit: Jaisen Mathai CC BY.

I’d eventually miss the free lattes I enjoyed at Yahoo! but my body was probably better off.

@collinstm 80k calories in my first year at Yahoo! via white chocolate mochas.
— Jaisen Mathai (@jmathai) June 26, 2012

In The Beginning was originally published by Jaisen Mathai at Jaisen Mathai on July 01, 2011.