Exploring America: Northeast, Midwest, Ontario, Quebec

This outlines my three week roadtrip taken in August 2025. Each section has a succinct summary which pictures, video, and audio files adding context to each destination. There is also a dropdown “Details” subsection for each section which includes deeper context.


Background

After getting laid off from my job at a health-tech start-up in June 2025 and receiving a last minute invitation to a family wedding in Michigan, I decided to take advantage of my time (and the wedding destination) and take off on a three week road trip in August. I planned to travel from Cambridge, MA through the Midwest arriving in Michigan and then returning through a few Canadian cities and Vermont to arriving back home in Cambridge.

Details

In June 2025 I was laid off from my first job post-college. I spent the first month scrambling to launch a SaaS (software as a service), trying to make money on the side doing personal training for soccer, and continuing to edit my podcast The Walk-On Way while taking advantage of time with two friends who had moved in with my roommate and I for the summer.

After a month of finding some success with the personal training business and zero financial success with the SaaS product – a lineup selection and recruiting data tool for college soccer coaches – I elected to take a road trip. I’d had the idea to travel across the country since graduation. I wanted to explore every US city that I felt might have potential to live in and see it for myself, with the hopes of determining a final “home base”. After taking a job directly after graduation, this plan was postponed to the Summer of 2026, when the World Cup would be hosted in the United States. I figured I could travel to the same cities, catch a few World Cup games, and try to interview as many people as possible for my podcast; however, when I was laid off I figured there was no reason why I couldn’t just take a chunk out of that now.

Further I saw this as an opportunity to cross off a few things at once: travel, see my family in Michigan, do door-to-door sales for my college soccer product Best.XI (since I had pestered my potential clients in Boston enough) and interview new guests in-person for The Walk-On Way – it was a win-win-win-win.

Timeline

August 1, 2025: Cambridge, MA

My final day in Cambridge involved some cold outreach and applications for a new job, an introduction to the Augmentation Lab1 at one of their “Hacker Houses”2, and a night out in Cambridge with a few of my friends two of which were also soon to be kicking off journey’s of their own with trips out to California.

Highlights:

Augmentation Lab’s Harvard St. “Hacker House” Demo Night
Details:

This section will typically include deeper detail into each stop. There will also be details for three themes of my trip: city impressions (would I want to live here?), Best.XI cold sales (documenting my attempt at cold selling a software I developed to see if entrepreneurship is a viable path for me), and neurotech networking / job hunting (documenting me walking into offices of business owners and professors to meet them or ask for work).

City Impression: This day marked about 1 year in Cambridge. In that year I’ve understood Cambridge to be a fairly granola, very liberal, academic hub. The neighborhoods definitely have distinct personalities with Harvard being the most touristy and a not-insignificant amount of residents emitting “walls-up” personalities. Lots of cardigans and more traditional attitudes. Central and Porter have more normal urban populations with academic residue from the nearby universities. MIT/Kendall has a more open, tech-centric vibe but has less residential soul than Harvard and other parts of Cambridge. I find it to be a great medium / transition-town to live in between small town living and moving to a bigger city and has really strong ties to health-technology and academia.

Best.XI: In the weeks leading up to my departure, I made stops at Boston University, Harvard, Boston College, and Northeastern. I was able to get face-to-face with all but Northeastern, with BU showing the most interest but none committing to a purchase.

Neurotech Networking / Job Hunting: During these weeks I was feverishly applying to jobs at companies such as Neurable, WHOOP, 8Sleep, OURA, Harvard and MIT. I was able to go in person to all of the local ones (ie. all listed except OURA and 8Sleep), and received numerous rejections with only a potential lead for unpaid labor at Neurable.

August 2, 2025: Woodbury, CT

My first stop involved a trip to neighboring state Connecticut. My parents were gracious enough to allow me to borrow their camper van for this trip while they were on an adventure of their own in the Canadian river systems.

I spent one night in Connecticut getting lunch with my granfather, packing the van, and watching a live stream of Vermont Green FC claiming their first ever USL2 National Championship.

Highlights:

Prepping the van and excitement for the trip.
Details:

City Impression: Northwest Connecticut is quiet and green in the summer. It’s a great respite from city-life but can be isolating and too slow. Great to grow up, not great for your twenties.

Best.XI: N/A

Neurotech Networking / Job Hunting: N/A

August 3, 2025: New York City, NY

The following morning I took off to New York City. This was a challenging first experience driving the van with low bridge clearances, lots of traffic, and aggressive drivers.

Highlights:

NYC skyline at sunset
Recording podcast with Jack Loura in the Palisades State Park with G.W. Bridge as backdrop
Details:

I elected to spend the night across the Hudson in Jersey City, NJ at the Liberty State Park. I parked here during the day, ferried in and out of NYC, and spent the nights stealth-camping in an upscale New Jersey neighborhood – Westfield.

My time in New York consisted of biking the West Side Highway, playing pickup soccer, getting lunch with high school friends, trying unsuccessfully to walk into 8Sleep’s offices to drop off my resume, interviewing NYCFCII player Jack Loura for my podcast and getting a tour of Manhattan by my old friend and Jamaica Queens-native, Cristian.

Ellis Island was particularly interesting to see in person. Although I didn’t ferry over, the weight of it’s history was fascinating to feel in person. Seeing the Statue of Liberty was also surprisingly inspiring.

City Impression: This place is HUGE. I was struck and overwhelmed with the mass of people I passed biking on the West Side Highway on Sunday evening. It certainly had everything you might need, but the people seemed physically weathered, even aged, from the hustle of the city. It was not particularly clean, but the views of the skyline and activity on the waterfront were amazing. Would not live here for a stretch longer than 3 months.

Best.XI: I tried to go to Columbia but it was an absolute fortress with walls all around and security at every entrance. I also failed to take into account how long it would take to get around the city so I was unable to make it to Fordham or St. Johns.

Neurotech Networking / Job Hunting: I tried to go to 8Sleep (a mattress cover product that helps regulate your sleep) but I was firmly stopped at the door. I tried leaving my resume at the front desk but they wouldn’t let me. I called customer support to try to weasel my way into a conversation about a job and was on hold for 30 minutes before throwing in the towel and heading to lunch with friends. Their is a big presence here with companies like OpenBCI, Cognixion, and Precision Neuroscience so a return will have to happen.

August 5, 2025: State College, PA

With a late start leaving NYC, I realized I wouldn’t make it to Pittsburgh at a reasonable hour so I decided to pit-stop in the middle at Penn State University in State College, PA. I expected this to be a stop-sleep-go situation, but I ended up having one of my best experiences here.

Highlights:

Driving to Pennsylvania
Josh, Anthony, myself, and Jackson (left to right) at Bill’s Pickle Tap Room during their Tuesday “Country Night”
Details:

I pulled in around 8pm and immediately went to see if I could manage to see the Football Stadium. I was greeted with bright lights coming from the stadium and a minor league baseball game at PSU’s Lubrano Park. After checking out these facilities I decided to grab some food and head to bed. I drove to the tiny downtown area, parked on a side street and headed into a nearby Target that was open late. It was a ghost town. I returned back to my car and heard a surprising amount of activity coming from a storefront, I walked by saw a bar that was shockingly active for an empty college town at 11pm on a summer Tuesday. Naturally I walked in and sat at the bar. I struck up a conversation with two young women seated next to me who promptly stood up in left. Shortly after two college guys came to order a drink next to me and within minutes we had assembled a crew and taken over a corner of the bar. Three hours later the bar was bustling and I headed home after a great night filled with countless failed conversations, a casino-salesman getting ejected from the bar, and a newfound admiration for the PSU culture.

The next morning I met some PSU soccer players while trying to contact their coaches about my software and had an amazing conversation with a few researchers at the University focused on wearable technology sensing. I capped off this stop with a visit to a family friend Mark Mennin’s sculpture at the University’s botanical garden followed by ice cream at PSU’s own dairy bar.

City Impression: State College is fittingly named because the town is literally just the state college. There is seemingly zero activity in the summer. The students that did linger had an admirable school pride and ferocious affinity for alcohol. They were generally welcoming and a very good time. Would definitely visit again for a college gameday.

Best.XI: I tried to catch the coaches in person but was only able to reach a few of the players who I asked to refer me to the coaches. I left a note in the door and a few follow up emails but at the time of writing this I have not heard back.

Neurotech Networking / Job Hunting: I met with Penn State researcher Dr. Farnaz Lorestani and was graciously shown around her lab before a great conversation about her research and how she hopes it will break into industry.

August 6, 2025: Pittsburgh, PA

I arrived in Pittsburgh on a Wednesday night found a nice quiet place to park on a cobblestone road on Carnegie Mellon’s campus. Pittsburgh served to be a productive stop in a city I have been hearing so much about as an affordable destination for young professionals.

Highlights:

Tour of Pitt soccer facilities with Pitt Women’s Soccer Head Coach Ben Waldrum.
View of the Ohio River from Duquesne campus.
The Cathedral of Learning
Details:

Pittsburgh left very positive first impressions on me. The first day was spent largely in and around the Pitt and CMU campus’s which boasted beautiful architecture, calm streets, and quiet neighborhoods. The area had a strong medical/health presence due to the Pitt hospital and I was able to learn a bit about this from a social worker I ran into on the street, Kate.

Day two, which included a night out in the “Strip District” and Pittsburgh’s downtown, revealed more of the city. I met some great people including another traveling software engineer Lazarus, a Pitt dancer Tara, and a hodge-podge of people in downtown Pittsburgh, including a Cowboy, a duo of Midwest girlfriends, a duo of Midwest mid-twenties pick-up-artists, and a couple of river boat party girls.

In between the downtown area and the college part of town was a more depressed, very industrial area that seemed to comprise much of the city. People I met while out at night advised against certain areas for safety. Otherwise there was some beautiful infrastructure and it seemed like strong community engagement in and around the college campuses.

City Impression: This a medium-sized city with small town vibes. The people here seemed grounded, generally keeping to themselves. I felt it was harder to gain acceptance hear on my night out then in Penn State. I would certainly live here if attending a program at one of the universities but the glaring disparity in wealth in adjacent neighborhoods was off-putting.

Best.XI: I had great visits to both Pitt women’s soccer and Duquesne men’s soccer. The head coach of Pitt, Ben Waldrum, and the assistant coach of Duquesne, Grant Glorioso, both seemed interested in the product. I sent follow-ups to both and haven’t yet heard back.

Neurotech Networking / Job Hunting: I had a GREAT conversation with Dr. Chris Harrison of Carnegie Mellon’s Human-Computer Interaction Institute and tried to make inroads at Pitt with Dr. Tracy Cui (Director of the Neural Tissue/Electrode Interface and Neural Tissue Engineering Lab) but was blocked at the entrance. The security kindly let me leave a note.

August 8, 2025: Columbus, OH

A late departure from Pittsburgh landed me in an Ohio State parking lot late Friday night. Much of my time in Columbus was spent at or around the Ohio State campus due to a hackathon I was participating in over the weekend so I didn’t get much feel for the city.

Highlights:

Capping of a night out in Columbus at Ethyl and Tank with new buddies EJ and Pete. Moments before being attacked on my walk home.
Details:

After my late arrival I had to have a quick turn-around with a remote Hackathon that Saturday (August 9, 2025). It was at this point where I really lost some steam in the trip. I procrastinated, lost motivation, and ended up not even submitting my Hackathon project which was supposed to be a 24-hour work session. I called it quits on the project and headed to catch some of the Ohio State soccer exhibition matches where I met some students who recommended some nightlife to me. I followed their advice and ventured to Short North Columbus.

I started off with Short North Pint House where I met an interesting guy working as an electrical engineer on the mega data-centers being planned by companies like OpenAI, Facebook, etc. I was astounded by his reported salary and felt insecurely compelled to leave the bar right then and try to make some money. Driven perhaps by this insecurity in tandem with continued struggle to break in with the people at this bar, I decided to go to another spot down the street – Standard Hall. Here I felt more accepted and was met with a more lively, welcoming crowd and had a great time. I decided to close the night with one more spot closer to my sleeping spot on Ohio State’s campus. This ended up being a great time, a nice dive bar and a newly assembled PSU-esque crew with Pete and EJ. I called it quits before close and headed home to end the night, but a small pack of belligerent 19-year old boys decided to try to initiate a fight with me. Fortunately, I was able to diffuse and avoid any attacks after being followed for a few blocks. All in a day’s work – great night!

The following morning I stopped by the Ohio State soccer offices once more and met a women’s player Nette who guided me to the empty coaches offices where I was able to leave a note to the coaches. Following this, I went on a last-minute bike ride along the river in Columbus to try to salvage a win out of what was so far the worst stop of the trip and was pleasantly surprised by a great bike path, an incredibly diverse farmers market and an up-close view of the Columbus Crew stadium.

En route out of Columbus I also stopped at Dayton and was pleasantly surprised by the city which came across as artsy, welcoming, and active.

City Impression: I unfortunately didn’t get into the city besides downtown and campus so I really don’t have much of an opinion here and I feel my sentiment was soured by the teenagers who tried to jump me. That said the town was quiet near campus given it was summer, but the young people out at night seemed more conservative-presenting (which to me means more traditional, slightly more stand-offish to strangers, and slightly more formally dressed). Nobody I spoke to that lived in Columbus was over the moon about it. From what I have seen I would not choose to live there, but the nightlife was actually excellent.

Best.XI: As I mentioned above I stopped at the coaches offices and left a note. I could have tried to get the coaches attention after the game, but kind of chickened out. I followed up but have not heard back from the men’s or women’s coaching staff. I also stopped at Dayton and met some of the assistant coaches who directed me to an email follow-up which I have not yet received a response to.

Neurotech Networking / Job Hunting: I did not speak to anyone. The Hackathon would have been a great opportunity to meet people and build my portfolio but I bottled that one.

August 10, 2025: Indianapolis, IN

Pinched for time I had to shorten my Indianapolis stint. I arrived at Butler’s campus in the northern outskirts of the city and met some of the friendliest people on this stop.

Highlights:

Learning the life story of Tomie who chatted with me for a couple hours by the van after his evening security shift at Butler University. His favorite phrase through the conversation was “Lemme tell you sum Tuck”.
Butler Bulldog statue by the field where I got to play soccer with some amazing IU Medical School students during there orientation week.
Details:

I got to Indianapolis and parked downtown. I did some research on a brief walk and decided parking at a university would be better. I landed in Butler at their athletics parking lot and met the security guard Tomie. We were both overlooking the field at a group of players and he was deciding whether or not to kick them off the field. We got to talking and he began to share stories from on the job. I ended up leaving to go play pick-up with the group, which ended up being a group of IU med students. They were very kind to let me join – special shout out to my guy Aaron who asked if I was vlogging this trip. No but that comment and similar ones from others inspired this blog post. Hopefully this is sufficient.

I ended up returning to the van after and catching up more with Tomie who told me his history of a decade of addiction, overcoming that addiction, the pride that came with that, and his gratitude for his new life with his kids and parents. He was a gem of a guy and so fun to talk with.

The next morning I headed to Butler’s campus after talking to some of the soccer coaches and caught up on some email and admin work. I then hit the road for Chicago, but made a stop in Indianapolis to try to get ahold of the IUPUI coaches.

City Impression: Butler was very nice with polite community members and a very well manicured campus, but everything did seem a bit plastic. I barely went into the actual city of Indianapolis except to stop by the IUPUI campus. The area gave off the vibes of exactly what I expected the midwest to be. I would need to go back to get a real impression

Best.XI: I stopped in the Butler men’s soccer coaches and was told that they had zero money in their budget and to circle back in the spring. I met one of the Butler women’s soccer players Lucia and she put me contact with the women’s head coach. I have not heard back. On my way out I met the founder of the IUPUI men’s club soccer program and he directed me to the varsity coach’s offices where I dropped off my Best.XI note to an empty office.

Neurotech Networking / Job Hunting: N/A

August 11, 2025: Chicago, IL

Despite to Chicago in the midst of a rainstorm, it lived up to all expectations. The inviting lake, big city opportunity, and a handful of resident friends made for an amazing stop in the Windy City.

Highlights:

Details:

My arrival in Chicago kicked off with a brief hyrdoplane through the city before arriving in a small neighborhood between North Park and Little India in Northern Chicago where my friend from High School, Sam Johnson lives. He lives with his girlfriend Cece and they were simultaneously being visited by our mutual friend James who was on a road trip of his own to all four towns called Geneseo in the US. Upon arrival I was welcomed to a showing of Netflix Original “Poop Cruise” which had us so entrenched that we decided to follow it up with “Zoolander”. It was great.

The following morning we went off to climb at an incredible rock climbing gym near Wrigley Field, then jumped in Lake Michigan, got a bite with some of Sam’s Chicago friends, and ended up watching the White Sox take down the Tigers at Rate Field in South Chicago thanks to tickets from my college friend and club soccer teammate, Antonio.

The following day I took off North to Evanston to meet with the Northwestern soccer staff and researchers. En route to the soccer offices I stumbled upon “The Garage” – a Northwestern incubator space for student-led start-ups. I met a few very kind, big-thinking people including a young man Christian who had just started a clinical motion capture start-up. His enthusiasm was infectious. After that, I continued on to try to meet the soccer staff and researchers at Northwestern, Loyola, and DePaul before meeting up with Antonio for a great run and jump in the lake. He had recently run an Ironman and was kind enough to let me keep up as he gave me some great advice on sales and life updates from his first two years in Chicago.

Following this I got some deep dish pizza and tiramisu and ate in in my van while watching Wedding Crashers. This was my pre-game to go visit my friend Sam on his shift at his bar “The Original Mother’s”. We had a great catch-up and talk in the quiet Wednesday night streets of Chicago before I said goodbye and headed home before leaving early the next morning.

On my way out in the AM I did sneak in visits to UIC and UChicago which led to a very late start en route to MI to see Grandma…

City Impression: Big city, with big city opportunity and activities but much more grounded and feels less hectic/hurried. Very accessible outdoors with clean swimming right off the shore of the city. I was warned of the dangerous neighborhoods of Chicago and while I did drive through some areas that I wouldn’t like to walk around in, I was not convinced that it was worse than other major cities. Would live here.

Best.XI: I was greeted kindly by Coach Payne and his staff at their wonderful soccer facilities and received some wonderful feedback on what could be improved to get them to buy Best.XI in the future. I continued on to Loyola, which – like Northwestern – had one of the most beautiful lakefront campuses I had ever seen. Here I was able to chat briefly with Brady, an assistant coach with Loyola women’s soccer. I followed up on email and haven’t heard back. Finally I went to DePaul and was stopped at the door but allowed to leave a note for the coaches at the door. I haven’t heard back. The following day I was able to get in with the UIC coaches. They showed me AMAZING hospitality, treating me to lunch and greek coffee. Minos, Sean, Alexyes, and the rest of the staff were incredible. They seemed very interested but no word yet.

Neurotech Networking / Job Hunting: At Northwestern, I also got some face time with Dr. John A. Rogers of Northwestern who asked “How did you get in here? This is supposed to be a secure facility.” when I knocked on his door and asked for time. Despite this he kindly sat down with me. At Loyola I tried to get in touch with Dr. Vincent Chen of the Biomedical Engineering department but arrived at an empty office and tucked my note into his office door. On my way out of Chicago I tried to stop at Dr. Hananeh Esmailbeigi’s (head of UIC Wearables Lab) office – she was not there but I left a note in her door.

August 14, 2025: Saginaw, MI

The road to Michigan was similar to that of Pennsylvania, Ohio, and Indiana – acres and acres of flat farm land. Generous hospitality from potential clients in Chicago led to a late start and very late arrival to Saginaw. Grandma was displeased with my tardiness but was kind enough to stay up late and fix me dinner after I arrived.

Highlights:

Steak and Shake nutella milkshake. I’m uncertain if the meat in the cheeseburger was cooked, but this milkshake was the best thing I have ever had.
Details:

After heading to bed shortly after arriving, I spent the following day hanging around the house with Grandma. She was kind enough to fix me all of my meals and insisted that I don’t do the dishes – “if I need your help, I’ll ask” she’d say firmly but kindly. I got a heavy and appreciated dose of stories from her sailing adventures with my late grandfather (Papou) Gus, my Dad and his siblings antics growing up in Michigan, and ample commentary on the state of the world – “I don’t know what the world has come to” she said one time disappointingly. It was a treat to get to share a full, relaxing day hanging around with her. My Aunt Connie and Uncle Ron stopped by too and caught up and made plans for the wedding the next day.

The following day we left early for the wedding and I was greeted by my cousins Kelly and Jamey (the latter of which is the younger brother who was getting married). The brothers and their Dad, my Uncle Nick, were kind enough to let me in on their family tradition where all the men sneak off to share a beer with the groom to celebrate his last moments as an unmarried man. It was a very nice moment and I was grateful to be apart of it.

The wedding proceeded nicely and I was able to catch up with more friends and family before heading home early with Grandma, Connie and Ron around 8:30pm.

The following morning I went to church with Grandma (my first ever non-wedding church service) and was able to meet many members of her wonderful St. Demetrius Greek Orthodox Church community. Following church I packed the van and shipped out to Toronto.

City Impression: Saginaw has lots of open, sprawling farm plots. I didn’t interact with anyone here outside of my family. It comes across as what I’d expect a midwest town to be.

Best.XI: N/A

Neurotech Networking / Job Hunting: N/A

August 17, 2025: Toronto, ON

I left Michigan after Sunday Church and after a long 5 hour drive (along with a disgustingly large consumption of Tim Horton’s donuts) I arrived in the Toronto suburb of Port Credit, where I would stay the night in the town’s marina parking lot.

Highlights:

Mucci and Kurt of Port Credit Athletics gym.
Details:

Upon arriving in the Toronto area, I elected to spend the first night in Port Credit, ON, a port-suburb south of the city. This was a classic boating town with nice ice cream shoppes, small downtown boardwalk, and a nice lakefront walking path. I stealth camped here in the marina and had no issues.

The following day I headed into the city parking at a park lot by the water and biked into town. I was a bit aimless and low energy at this stage of the trip. I explored an underground mall, met a stranger who was also traveling and explored the UToronto campus with her, and then returned to my car and went on a run and bike ride along the river. While running I met a Ukrainian women Kristina who had moved to Toronto at the start of the war.

I returned to Port Credit to rest and returned again in the morning. On my way North back into the city I stopped at a gym (Port Credit Athletics) to shower and workout. I met the staff Kurt and Mucci were very kind to be curious about my trip and give recommendations for Toronto. But Kurt lowkey forced me to give them a good Google review. Was a good gym – crossfit style – but outdated, not very clean, and crammed equipment. My Google review says otherwise.

City Impression: I was in a bit of a bad mood as I was abstaining from caffeine and going through minor withdrawals so my opinion is likely biased. I felt the city was nice with a great lakefront running and bike path; however, the water in Lake Ontario at least near the city was far murkier and less appealing than that of Lake Michigan. Further, the people seemed more stand-offish and didn’t have that trademark Canadian kindness (at least those that I talked to). This could also have been my own projected grumpiness. I would not live here.

Best.XI: N/A

Neurotech Networking / Job Hunting: I tried to meet with two UToronto researchers: Dr. Steve Mann (“Father of Wearable Computing”) and Dr. Alex Mariakakis (head of the Computational Health and Interaction (CHAI) lab). Steve was not in his office so I left a note. Alex’s online listed office was a conference room, so I just hung around there for a few minutes and then saw someone walking out of the bathroom. I had only seen his picture once so I wasn’t sure but I asked if he was Alex and sure enough he was. Alex kindly invited me into his office and we chatted for half an hour or so about his work and the future of wearables.

August 19, 2025: Ottawa, ON

Highlights:

Happy Goat Coffee Company. This place was awesome.
Details:

I approached Ottawa late on Tuesday night so I decided to stop in a nearby suburb in case parking in the city was busy / unsafe. I decided on Arnprior in an apartment complex lot by the river.

The following morning I went to Robert Simpson Park and went for a run and swim in the Ottawa river. The water had a iron-red hue, but felt clean. I spoke with a couple locals: one was a man who spotted my Vermont Catmount shirt and told me of a property he just sold after 20 years in St. Albans and another was a woman with the cane who explained how normally there are more mallards than the few we were looking at floating in the lake. She continued with how she wished she could have seen the area we were in before humans manipulated it.

I left shortly after and made it into the actual city. The drive in was gorgeous with green parks, river views, and a nice, clean-looking entrance to the city. I parked on a side street and walked around the city, before landing in the UOttawa Engineering building to catch up on emails and my Best.XI CRM. I got dinner at a chain Mexican place and walked around Strathcona park which had lots of people chatting in small post-work groups, a live outdoor theater, and runners and bikers moving along the river. I then biked downtown during sunset and headed to bed where I was parked on the street in the Sandy Hill neighborhood of Ottawa. This was the most urban I had parked and I definitely was more restless with cars zipping by, late night folks walking by chatting, and at least one instance of a tug on one of the van doors.

The next morning I stopped at an amazing coffee shop – Happy Goat Coffee, and headed out on my last stretch of the trip.

City Impression: Ottawa at first exposure seemed like a little Utopia. lots of space, small town vibe in a city and an active-looking population. The city looked clean and quiet. The only thing that challenged this was a bike through the downtown / nightlife area on that Wednesday night. There was a surprising amount of homelessness and evident drug use on the streets just blocks from the utopia-esque area. A few people I talked too seemed to feel like Ottawa was just a pit stop and not a suitable place for young people – if nightlife and dense populations are important, I could understand.

Best.XI: N/A

Neurotech Networking / Job Hunting: N/A

August 21, 2025: Montreál, QC & Burlington, VT

I left Ottawa in the AM and headed to Montreál with a plan to stay the night and head south the following morning. I ended up only staying the day and heading to Burlington, VT to spend the night instead.

Highlights:

Mont-Royal city view
Details:

This was a big day of travel. In Montreál I had planned to see my friend Danny over coffee but a fender bender accident delayed him and my own moronicity led me to biking across town to the wrong coffee shop. We postponed and I headed out of town south to Vermont.

I arrived just in time for UVM’s home opener soccer game against Sacred Heart where they won 2-0. Following the game I caught up with parents and old teammates and then headed to bed.

The following morning I stopped in my old office (where I was laid off) and caught up with my former mentor and co-workers who were amidst a big push to stay afloat. I think they’ll get it done. Then I was able to stop by and see both of my siblings before heading south once more.

City Impression: Montreál in the summer is one of the best cities I have ever been too. Lots of outdoor activity, beautiful architecture, Mont-Royal as an in-city hiking, running, and biking hub, a fully European-feel, multi-lingual, and very beautiful people…

Burlington is always a gem. Very granola, amazing lake view and lake activities, ample outdoor accessibility, decent entrepreneurial culture for the size, access to amazing skiing. Having lived there for 4.5 years, it also has a disproportionately large unhoused population, can be a dangerous echochamber for young left-leaning people with no real world-experience, and, while posing as very accepting, can be home to many non-inclusive non-traditional groups: crunchy douchebags as I call them. This is largely around the skier, mountain biker, etc. culture. FYI this is presumably the minority of these groups but was one of the drawbacks of the town in my eyes.

Best.XI: N/A

Neurotech Networking / Job Hunting: N/A

August 22, 2025: Woodbury, CT & Cambridge, MA

After finishing up in Vermont, I headed home to drop off my parents van, clean it, lock up and head home to make it for my conference the following morning.

En route south through Vermont I made some procrastinatory stops and finally arrived in CT at 8:00pm. The van cleaning and unpacking took much longer than expected. I left around 10:00pm and arrived in Cambridge just after midnight, concluding my trip.

Highlights:

Recording an episode of The Walk-On Way with the Vice President of US Soccer Nathán Goldberg-Crenier at the Harvard Kennedy School.

Lessons Learned

  1. Just show up. Applications and emails are stupid. If you want something, go show up at the door and ask for it face-to-face. People are quick to ignore you over a screen; very few people will physically slam a door in your face (even if they want to…). A request for two minutes of someone’s time when you are right there in front of them is frictionless for them and will seldom be rejected. This theory was validated by me getting in rooms with people that I have no business talking to (like Chris Harrison of Carnegie-Mellon, John A. Rogers of Northwestern, and Pedro Lopes of UChicago). Further, this technique is exactly how I got a job at my first-choice company, Neurable, during a down market and when they were “not hiring”.
  2. Travel with structure. Having a focused (but not suffocating) scaffolding (like my Best.XI cold sales and neurotech cold networking) makes travel feel much more purposeful. I feel that this is due to a few reasons:
    • At times during my travels, I had moments of “What the actual fuck am I doing out here?” while wandering through random towns in the Midwest. This was largely a comparison trap. My friends are in the big city making money and I’m in Dayton, Ohio paddle boarding in a sewage canal at 11am on a Tuesday. The scaffolding helped deter these feelings by having an answer to the “what am I doing here?” – “well, I’m here to try to sell my software to Dayton, see if I can talk to any faculty in BCI, and check out a new city.”
    • Structure actually leads to serendipity. Often times I would go to a professor’s office and they would not be there (Academics out of office in August!?!? Shocking, I know.); however, frequently there would be someone near by or an interesting office next door with a relevant title that would end up being an interesting connection. Or maybe the building that I saw out the window across the street looked interesting and I was led to an interesting sight. Putting myself out there in these situations NEVER (in this trip or in prior experience) led me to anything but good. The only bad has come by inaction.
    • This may be more personal, but when I have no structure I can sometimes feel unmoored. I have found that this disoriented feeling makes taking action challenging as I don’t know which direction to move in with conviction. Structure orients me in a set position (it doesn’t really matter where I am oriented in my opinion, just that I am) which allows me to move in a set direction with a reference point and end each day being able to measure progress or lack there of.
  3. People LOVE a travel story. Every reaction I got when describing my road trip was along the lines of “I wish I was doing that” or “Are you posting this anywhere? I’d love to follow the journey.” – hence this blog post… All the more reason to take unconventional paths, even if just smaller scale trips or unique experiences in town. People are drawn to that novelty and it makes making friends much much easier.

FOOTNOTES

  1. A “philosopher-builder” community born out of the MIT Media Lab and Harvard. ↩︎
  2. A shared house where young developers come to live and code. Often a place where start-ups are born out of. Popularized in Silicon Valley. ↩︎

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