Last year today I embarked on an epic rail journey from Montreal to Chicago via Vancouver and Seattle.  This time of the year is pretty much the only time I can completely escape startup life (and Internet connectivity), and a year ago I seized the opportunity to do something I'd been dreaming of since childhood: take "The Canadian" across Canada. Sat down with a beer and watched my videos from that trip (see playlists below) which brought back very fond memories not only of the trip itself, but also of Startical 1.0 which involved a similarly ridiculous Montreal to San Francisco rail journey. The playlists: "The Canadian" - Toronto to Vancouver by rail "The Empire Builder" - Seattle to Chicago by rail Also reminds me of my  Rails and Reels: History, Infrastructure and the IoT blog post from 2013, just after we had become "World's Best Startup".  Somehow rail journeys bring out the philosopher in me...

There was fugly wallpaper on BOTH of those walls... ...the last to (soon) be painted white. Only just today realised that our new office, which is on the corner of Sherbrooke and Parc streets (Parc is French for Park) could cheekily be called PARC.  XEROX PARC (Palo Alto Research Center) is effectively the birthplace of much of the core technologies we continue to use today (tablet computers, graphical user interfaces, mice, object-oriented programming...).  See this reelyActive blog post .  I've been calling the office Sharc to date, but PARC is not only awesome, but also fitting since the intent is to use it as a living lab and showcase of all the emerging tech we have developed and continue to develop. It may seem silly, but this is the highlight of my day and unbelievably motivating!

It's rare that I can justify an entire day to reading.  Being on the mend from my cold, and not being in a state to be efficient at much else, I was somewhat able to justify taking the time to read Kauffman's A World Beyond Physics just about end-to-end.  Although at many moments along the way I felt guilty about all the other things that I was "supposed" to be doing. Nonetheless, the timing of this read was brilliant.  I've always been fascinated by evolution and emergence and the broader application of these concepts.  I read Kauffman's 1996 work, At Home in the Universe, and this latest (2019) work attempts to add the missing piece in his theory of the emergence of life as we know it. I realise that reading helps me cope with a distinct loneliness I feel.  In continuously advancing toward the vision of reelyActive (my startup) I get further and further away from what might be considered the normal or established context.  In other word

Of course I pushed too hard and paid the price of feeling that scratchiness in my nose by mid-morning.  At best I was gonna carry a mild cold through the holidays.  At worst I'd be a write-off for an entire week (which happened to me right after Christmas in 2015). It's not difficult to realise that I pushed too hard.  Despite being on Startical with its explicit guidelines , there was just way too much to get done before the holidays.  Even my Startical posts for nearly the past week have been placeholders to fill in later.  And now that's caught up to me and I'm starting sniffles. The challenge now is striking the optimal balance between preventative care and completing my commitments before Christmas: sending out personalised Owl-iday e-mails including the Owl-iday Special I had worked so hard to create.  I think I'll err on the side of preventative care as I really don't want to wrap up Startical feeling sick and useless...

...so what is it being invested in? Received an unexpected call from a candidate investor this morning, and in our discussion, by far the most striking thing he mentioned was how there is more money in this world than there has ever been. That's something I think about a lot and is one of the things that leaves me scratching my head.  If there is so much money in the world (and there is, even if it is all fiat money ), and all that money is searching investment in which to grow, how is this not a golden era of innovation, with technological and social innovation companies blessed with liquidity to create new value for exploitation? I could write a book on this subject (actually, a few years ago a registered the domains make-money-not-progress for this exact purpose), but won't do so here.  I will just use the occasion to document how frustrated I am with the hypocrisy and inefficiency of the current economic paradigm.  When I have frank discussions with my colleagues on b

Woke up at 6am.  Walked dog to rental truck.  Filled truck up with fuel.  Drove truck back to U-Haul just in time for 7am opening.  Continued dog walk.  Arrived at locksmith just before 8am opening.  Made copies of office keys for coworkers.  Popped in to office store and picked up gift wrapping paper.  Home and ready to make breakfast at 8:15am. I take much pleasure in accomplishing travelling-salesman-like challenges such as these.  Probably the key takeaway from Startical 1.0 was my propensity for " creative optimisation ".  This morning was exactly that, and it was fulfilling.

Almost match the original black, orange and red colour scheme...

Gratuitous dog pic.

Context switch.  Mission accomplished.

Thrifting with niece, new office.

Video link to come...

Answers to the question from Vaughn and Noor.  Art with Eva...

Experience, knowledge transfer, getting the job done...

My good startup buddy Suzanne reached out to say hi, and of course I asked her the question: if you had one extra hour per day just for you, how would you spend that time? I would collect all those hours until I had enough to take a trip. Somehow it doesn't surprise me that Suzanne would be the one to push the boundaries on a proposition as straightforward as one hour per day.  While I see that as a violation of the simple principles of the extra hour per day, it's great to challenge my own perspective.  That's what I love about unabashed entrepreneurs!

Attended the Christmas cocktail party of TechnoMontreal, a non-profit technology cluster in which reelyActive participates.  Ended up having a great conversation with the Chief Information Security Officer (CISO) from a long-established company and the marketing lead for a non-profit.  Despite the differences in our respective organisations, we had no difficulty finding common ground on the fact that it is difficult (and lonely!) to advance a progressive agenda!  There is no shortage of resistance to change. This reminds me how important it is to find occasions to interact with people just outside one's usual circle.  If you're constantly surrounded by people who are participants in the same game as you (ex: tech startups) it's easy to accept the dynamics of that game as normal.  Stepping outside of that circle, it becomes clear to see what aspects are unique and common to each game.  And such wisdom is critical when trying to affect change!

Got caught up on business matters with my friend and colleague Juan.  During Startical 1.0 , I had yet to meet him in person, but he had this lovely message for me back then.  Juan and I have lived some difficult entrepreneurial struggles together, and have had shared some unconventional business travels together, so I was very curious how he would respond to the question of how he would spend one extra hour per day if he could use it however he wants: I would use the hour for introspection, to work on my own shit, to read, to write and to learn. Juan said he was already making time regularly to do this.  He said it's easy to forget to make oneself the priority.  I definitely agree.  Introspection was part of a key takeaway from Startical 1.0 and is clearly a theme here once again!

Here's a sneak preview for those who are following Startical 2.0 in real-time: Owl-idays 2019 .

This will likely be the click-baitiest post title of Startical 2.0, but it is in fact the title of the film I watched on Netflix while taking a lunch break.  And it was good. If you haven't yet seen it, let me perhaps surprise you with the seven fundamental tenets of The Satanic Temple: One should strive to act with compassion and empathy toward all creatures in accordance with reason. The struggle for justice is an ongoing and necessary pursuit that should prevail over laws and institutions. One’s body is inviolable, subject to one’s own will alone. The freedoms of others should be respected, including the freedom to offend. To willfully and unjustly encroach upon the freedoms of another is to forgo one's own. Beliefs should conform to one's best scientific understanding of the world. One should take care never to distort scientific facts to fit one's beliefs. People are fallible. If one makes a mistake, one should do one's best to rectify it and resol

It's Saturday morning which again means I let myself decide what I want to work on.  And I wanted to write a post for the reelyActive blog so I did: Open hardware: closed case? I suppose my writing skills are limbered up from all the Startical posts because, much to my satisfaction, I was able to crank out the post in time for lunch.  And I'm really proud of how the header photo (above) turned out.  It wasn't planned to look like an enclosure eating a PCB (or sticking out its tongue, depending on your perspective) but rather the concept emerged.  I already feel a sense of creative accomplishment today!

...at least according to the fortune cookie! Today the team and I had lunch with a first time tech entrepreneur with whom we've crossed paths at several recent events and conferences.  We were pleased to share our experiences with him and answer his questions.  Not only that, we took away a lot from the discussion and his experiences too! After lunch, I met up briefly with my friend and collaborator Evelyne to plan for our upcoming office move, and asked her the question: what would you do with one extra hour per day just for you? She answered three things: Listen to music, go out for coffee, and pet my bunny. Seems there's a trend where those most committed to entrepreneurship and/or their families would spend their hour on personal development of some sort.  Indeed, it is important to take care of oneself!

Was rewarded with this beautiful morning full moon on the 6:30am dog walk.  Thought about how excited I was to have a productive day today as yesterday I didn't advance anything on product, even if I did have some very important meetings and completed both gift and grocery shopping.  I'm also motivated to get caught up on my Startical writing this morning too.  It is incredible how much context-switching my mind is constantly undergoing, and I'm afraid that when I don't capture my Startical thoughts immediately they may distort or even vanish. If I had an extra hour in the day during Startical, I would surely use it to keep up to date on my Startical writings!

Attended the Salon des métiers d'art du Québec which is an annual event that brings together artists and craftspeople from across the province, and a great place to pick up unique gifts for the holidays. As the event is close to where I live, it has been easy for me to pass by each year, and as such, I appreciate walking through and recognising many of the artist-entrepreneurs I've spoken with and whose works I've purchased.  For many, their journey is not unlike that of a startup entrepreneur: they have a unique skill or insight, but in order to have a viable (let alone massively-scalable) business, they must continuously adapt themselves to the market and their clients. I bought a gift from a woman who earns her living as an architect, and takes pleasure in her creative work as a sideline.  She noticed my engineering ring and we had a great conversation about careers in design and technology.  It wasn't difficult to choose which of her works would make the best g

Had a quick catch-up call with Tom who was the first person to reach out to reelyActive on AngelList way back in 2012.  Over the years we've kept in touch and I consider him to be an outstanding mentor even if we only find the time to speak once or twice a year. It was Tom who suggested to me that I read Frédéric Laloux's Reinventing Organizations on a previous call after I explained to him my ambitious plans to avoid hierarchy and embrace emergence within our startup.  That's the same text I discussed with Cynthia and the same author I presented to Will . Tom was supportive of my Startical, reminding me how much he enjoyed and learned from his own three-month sabbatical not long ago.  Did his business fall apart during that time?  No.  Did he stress about that the whole time?  No.   Did he return to work motivated and refreshed?  Yes! I often feel quite alone and isolated in my thoughts and eccentricities, and it doesn't take much to begin to self-doubt: "

Adrien, who has a nice mention in Startical 1.0 , reached out to me that he was in town for the week.  So I joined him for an amateur comedy night in the neighbourhood where I completed my graduate studies and worked at my first startup.  I don't often get out in the evenings, as generally I'll be on my computer working on something, so this was a nice escape.  And it was great to catch up with Adrien who is no stranger to tech projects with the potential to scale big. I tested out the question of what he'd do if he had an extra hour each day to do anything he wanted.  He responded that he'd use the time to work on those sideline projects that could eventually spin off into a standalone business.  Makes sense.  Ten-years-younger Jeff would have responded to that effect too. I like this question!

A few months ago, while walking my dog, someone stopped me and asked if I would be open to a spontaneous interview in which I'd answer a question selected by the previous interviewee.  Today, I sat down for coffee with that person, Cynthia, to ask her a few questions about how to capture and share discussions and interactions as part of Startical. One of the ideas that came up was to ask fellow entrepreneurs a simple yet revealing question, such as: If you had one extra hour per day, just for you, how would you spend that time? I tested that on the team over lunch and the responses were: Read (as a way to have time by oneself) Read (for much the same reason as above) Get outside and explore/visit Cynthia's own answer was "sleep".  I like the idea of asking such a question and noting the response and will definitely test it out further in the context of Startical!

Worked on two creative projects today, both in line with the needs of the startup, and feel great about it. First, my colleague Camille and I discussed how she can evolve our monthly newsletter to maximise reach and impact, and to have fun creating each one.  Together we came up with some great ideas about starting with an iconic image/photo for readers to look forward to, and to compile the spoken version of the newsletter into a video with watch-worthy visuals. Second, I spent part of my evening writing an "Owl-iday Special" which is an annual tradition we started in 2017.  I managed to bang out nearly twenty verses of prose in rhyming Christmas classic fashion.  A combo of nerdiness, philosophy and tech trends with a humanistic touch.  What a delight! I recognise that the ability to mix creativity with work so fluidly is something I cherish.  I don't think most workplaces, startup or otherwise, would value and encourage this as highly as I do.  This aspect of my startu

Spent the entire day on the computer coding and it felt great.  I added features to the core product that any user would be able to acknowledge.  And I added a key page to the product website. This affirms for me the value of regularly achieving tangible milestones.  Today was a special day because there are several significant achievements.  But on any given day, even completing just one small but tangible milestone is enough to keep spirits high. Today's only downside is that these advancements were made at the expense of keeping up to date on communications, aka the dreaded e-mail backlog.  It's difficult to not let that affect me, even when I'm on Startical and my autoresponder states that I may take longer than usual to reply. Reading a book before falling asleep (my usual routine) helps a bit...

I spent my Sunday afternoon developing a web app called Hello Transmitter! for the startup's open source software suite.  And I enjoyed myself and am pleased with my use of my Sunday afternoon. I chose to do this because we have a demo coming up this week and I think this adds a lot of value, and will give me a strong sense of pride and accomplishment to show it off. As the web app is in a "good enough" state, I stopped myself from continuing to work on it into the evening, allowing my brain to enjoy one sleep before developing it further in the morning.  This gives me the chance to celebrate the second advent and reflect on my first week of Startical 2.0.

Spent the afternoon and evening with family celebrating my nephew's birthday and got to meet their new kitten for the first time.  She's super cute and energetic! I'm happy to note that I was able to disconnect completely from work for the entire day.  I'd say that's generally the case with family time.  Even spending a half-day every other week with family is an effective way to take a break from the startup, and that's an achievable schedule.

Well, this was a timely video that embraces many of the key aspects of my Startical, including the purpose of the startup itself and the business of selling what customers need rather than expect.  Justifies spending time on YouTube while eating lunch.

Since I adopted Obélix, our Saturday morning routine has been to take a long walk just after we wake up.  This Saturday morning was no different, and we chose a different route which offered a nice view of the sunrise.  As I mentioned on Morning One , my mind is free to wander during these walks, sometimes thinking about work, but more often not. On this walk I thought about what I'd like to do with my Saturday morning.  My normal routine is to enjoy a good breakfast and watch some political comedy, such as Bill Maher clips from the night before, to keep up with politics and (hopefully) enjoy a laugh or two.  Then I'm free to work on whatever I want to: I've come to use my weekends as an opportunity to advance on whatever matters most to me.  Almost like a two-day Startical without the writing and introspection. This particular morning I've decided it would be great to catch up on my Startical writing and introspection which I'm now doing...

A holiday memory from childhood is putting my boots in the entrance the night of December 5th before bed, and waking up to (hopefully) find chocolates, cookies and citrus fruits in them the next morning.  This is a celebration of Nikolaustag ( Saint Nicholas Day ) which has many interesting regional traditions. I decided to surprise my startup colleagues with cookies in their boots which were conveniently located, according to tradition, in an entrance before we headed out together for lunch.  Had they been naughty rather than nice, Krampus or Knecht Ruprecht may have instead placed a stick in their boots for their parents (or boss?) to beat them with.  Yes, that really was the darker side of the tradition although I only know of anecdotal accounts from the previous generation of this actually being carried out!

It was wonderful to have Will along for the first few days of Startical 2.0 given all the adventure time we shared together during Startical 1.0 , and now it was time for him to continue his travels. As he was departing, I thanked Will for his visit as it provided a rare occasion for me to discuss wellness and philosophy and share experiences (especially culinary) in depth for more than just a fleeting moment.  I realise that most of my time is spent with my startup colleagues or working in isolation.  In my twenties, it was relatively easy and common to spend a week with friends-outside-of-work, but as we've all grown older (and more responsible?) it seems increasingly rare to do this.  It's easy to find an excuse when you have a career and/or kids. This reinforces for me the importance of making time for visits like these, or adventures like the one I shared last year with Will: Montreal to Chicago by rail via Vancouver and Seattle. ( Photos |  The Can

Had a morning call with a friend from the startup community.  One of the first things he mentioned was that he left Paris for London on one of the last trains before the general strikes.  And that there was a fatal stabbing outside his London hotel the night before. It has been difficult to ignore the changes in the global political situation in the past few years, especially since 2016 with the Brexit vote, the US election, then months later the Catalan independence referendum and finally last year the Gilets jaunes in France.  I have close work and personal relations in all of these places. There's a lot of anger and frustration in the world of late.  And there are plenty of excuses to get angry and frustrated working in a startup.  Combining discontent from both politics and startups is a potential recipe for disaster.  I'm doing my best to balance staying informed yet neutral on politics.  And of course Startical 2.0 is about staying healthy and positive in my startup!

Emulate Showcase Kit.   That little dropdown button is what the user sees, and that's what I added to reelyActive's core open source software product today.  Of course adding the button was the easy part.  Adding the functionality, which involves architecture-level decisions, was the challenging part. I had been planning to complete this six weeks earlier, and the fact that I was effectively able to complete this in an afternoon made it frustrating that it hadn't been completed sooner.  However committing the code provided me a real sense of satisfaction. I wish I could write code and advance the core product whenever I'm motivated to do so (which is most of the time).  Unfortunately, my role in the startup involves many additional responsibilities, and I'm not convinced that I've been able to strike a healthy compromise between the two.  I think about this a lot and intend to dig deeper as Startical 2.0 progresses. Note to future self: this was starlin

Here's my e-mail autoresponder message similar to the one in Startical 1.0 .  Curious to see if it garners interesting responses like the ones received during Startical 1.0: "I would love to do the same … !" "C'est une bonne décision. L'esprit est aussi important que le reste et j'espère que ce Startical te permettra de recharger les batteries comme tu le souhaites."  "It’s what we all wish we could do!"  "Take a good rest Jeff, you deserve it" "Awesome auto reply"   

Will and I discussed finding the balance of progress and purpose in organisations (startups and otherwise) which reminded me of the book Reinventing Organizations by Frédéric Laloux which was recommended to me by one of my mentors.  We found the clip above on YouTube (if you're not familiar with Laloux, it's a nice short summary of his work) and one element stood out for me: what he called Evolutionary Purpose . How I understand this concept is that the purpose (or soul) of an organisation evolves over time, rather than an individual or leadership team directing towards a specific outcome.  It's very much in line with the sailboat analogy and the lunch discussion I had with the team. It is very reassuring to me that the people closest to me today all affirmed my feelings on leadership, and interesting that it often took very different paths/context for us to be able to truly connect on the subject.

A short walk from the restaurant is the Polytechnique Memorial, and as one of the topics at lunch was the challenges faced by women in engineering and entrepreneurship, we decided it would be worthwhile and respectful to visit as this week will mark the 30th anniversary of the Montréal Massacre. Bordering the park (on the left in the photo) is the office where I spent five years at the first startup I worked at in Montreal: Purelink Technologies.  I started there when I was Camille's age.  The walk gave me the occasion to share with my colleagues all the haunts and stories from that era. If I'm to sum this up in the context of Startical, there is much to be learned from the past, both good and bad.  As much as entrepreneurship encourages looking forward, it is healthy to pause from time to time and look back. "Those who cannot remember the past are condemned to repeat it."   —  George Santayana

Attended a client meeting this morning with my startup colleagues which we followed up with a discussion over coffee that we continued over lunch. I was happy to explain my Startical progress to my colleagues and share with them my motivations for embarking on this endeavour.  I shared with them the story Claudia had shared yesterday about teaching herself to turn off, and how I was reflecting on that myself.  It is difficult to find the balance of being a strong leader and evangelist of your startup (or project) and the humility of accepting feedback and even failure.  Said differently, there's a general reverence for the type of Steve Jobs or Jeff Bezos figure, yet I'm sure if you ask those who work(ed) closely with those figures, many would feel strongly otherwise. What I appreciate in our team is that everyone is open to taking the time to have these kinds of discussions.  And while we might convince ourselves that our time could have been better spent advancing t

Enjoyed a brief morning discussion with Will, picking up where we left off the night before, which I'd describe as the sailboat analogy: You can build a sailboat optimised for specific conditions, but as the wind and seas are variable, what really is optimal? Applied to startups, one might say this is the choice between building: a sailboat optimised for a sprint in specific conditions (i.e. quick exit), or, a sailboat adapted to operate in any conditions (i.e. cockroach), or, something in between My life experiences and upbringing have strongly inclined me to build a robust vessel that can navigate reasonably through any conditions.  However, I'm well aware that the shiny, fast sailboat is the one that garners the most attention in the harbour.  Few will be inclined to actively seek out the sailboat most likely to weather the worst storm. Then Will brought up a pertinent point: "do we really need to optimise for progress?"   In other words, should we p

Placeholder for challenging one's optimistic view of the future. Resistance to change. Meet the customer where they are. What are we trying to optimise?

Placeholder for scoping devops and cloudops role with Will: - empathise with user - because startup team is small enough, can arrive at consensus quickly and definitively - working with people you like, doesn't mean you have to be like-minded!

On the walk home from lunch, Will and I passed through the Marché Casse-Noisette, a Christmas market where local artists and entrepreneurs sell their work, and I was pleasantly surprised to bump into Claudia from Bijoutia who was a figure in Startical 1.0 ! She shared with us a personal story about the inability to turn off one's creative drive as an artist, and how she overcame this through meditation.  Curiously, she said that those closest to her showed concern for her when she was able to turn off temporarily, because they did not recognise her in that state! I think it is very much the same for startup entrepreneurs: it is often difficult to turn "off", and even if we are willing and able to do so occasionally, how might we be perceived by those around us?  Since Startical 1.0 I've been more comfortable allowing myself to turn off for up to a day or two when I feel it is essential for my well-being.  But I must admit that my greatest concern rema

This morning my sister reached out about having lunch together, and Will and I joined her close to her office. Upon reflection, living walking distance from downtown affords me the ability to take advantage of spontaneous meetings, both social and business.  I recognise how much location factors into well-being.  If I lived further afield, I would easily isolate myself by justifying passing up meetings such as these. One of the highlights of the lunch discussion for me was Will's interest in leadership, especially in the context of progressive organisations that seek to do away with hierarchy.  This reminds me of a great book that was recommended to me by a mentor: Reinventing Organizations.  We've had discussions in my startup about how we should organise ourselves and structure responsibility.  Being exposed to various organisational structures over our individual careers, it is difficult to align on an ideal for our own startup. Our discussion helped me recognise that as the

My colleague Camille from reelyActive joined me in decorating my Christmas tree.  It will be her first holidays in Canada, and I was glad she accepted my invitation to share in the tradition passed on to me. Better yet, my American friend Will, a central figure in Startical 1.0, drove up to join me too.  The timing just worked out great.  And I'm glad Camille and Will got to meet and exchange stories and ideas.  They set up the (Incan) nativity scene under my tree, with Caganer in the baxkground (a great reminder of my 2016 work trip to Catalunya - look up Caganer for a laugh about Christmas traditions!). We ate a great meal together, prepared by Will.  And then celebrated the first Advent, another tradition from childhood that I'm glad to keep alive.  I got to introduce the pair to stollen and schokoladen lebkuchen and other delicious treats that I grew up on. Too often my weekends represent an opportunity to catch up on work, generally in relative isol

Today being the first day of advent, when traditionally I set up my Christmas tree, I had a perfect occasion to drive out and visit my Dad who graciously hosts the tree and ornaments in his basement. It is a nice change of pace to spend time with my Dad.  We'll chat a bit about how my startup is going, but most of our time is spent chatting about anything but.  He cares very much that I have a reasonable level of financial security and I appreciate that he checks up on that.  Over the past 15 years working in startups, on so many occasions I've seen people make terrible decisions based on financial pressures.  I would be very disappointed with myself if I got to that point.  And honestly, I've been close many times since Startical 1.0. Just knowing that someone close to you truly cares about one of your greatest fears as an entrepreneur represents a huge pillar of unspoken support.  Lunch with Dad reminds me how fortunate I am to have that.

Startical 2.0 begins on a Sunday.  Woke up without an alarm clock at the weekday alarm clock time despite this being a good hour before December sunrise. The first thing in my daily morning routine is the dog walk, and this morning is no exception.  Bundled up for the cold and took Obélix for a 45 min tour of downtown as our usual route was blocked for construction (a common Montréal theme). I enjoy these morning walks, even in the dark and cold.  It's time where I'm not in front of a computer or mobile screen, but rather free to let my mind wander about.  This morning I thought about Startical.  I thought about Startical 1.0 and prepared myself to be in a mindset of following the guidelines for Startical 2.0. I'm excited.  It's a challenge in that it demands a lot of time for introspection and sharing, but I enjoy challenges and the motivation they provide.  So there we have the start to Startical 2.0 on what is now a sunny Sunday December 1st!