Wednesday, September 14, 2022

“It’s Like Going Back to the 90s” — INBOUND 2022 Trip: Part 2

The conference begins...

In my 2019 series of blog posts on the INBOUND conference, I talked about how young everyone seemed. I was 46 at the time, and felt like one of the few older attendees at the event (well...other than the speakers). 

This time out, there was a much more eclectic mix of demographics. Sure, there were still a lot of attendees under the age of 30. But my anecdotal evidence suggests this year's event felt like a more balanced professional conference with numerous attendees in their 40s and 50s.  

After getting a quick bite for breakfast at the Dunkin Donuts near our hotel, we headed to the BCEC for the first day of INBOUND programming. 

INBOUND had a different format for the sessions this year. The content was structured in either 30-minute sessions or 90-minute “deep dive” sessions. 

On the surface, the format makes sense. Some speakers/topics are better in bite-size chunks...while others require in-depth examination. 

We only attended two of the 90-minute sessions (which will be featured in the next blog post). The rest of the programming on our agenda was comprised of the 30-minute talks (some of the “deep dives” we wanted were full by the time we registered for sessions). 

The first session we attended on Wednesday was the HubSpot Spotlight featuring HubSpot CEO Yamini Rangan, CPO Stephanie Cuthbertson, and CTO and Co-Founder Dharmesh Shah. 

I guess I should mention that the INBOUND conference is put on by HubSpot (the company provides a popular CRM software product for marketing professionals).  

A key point of the session was how disconnected customers are these days, and how digital fatigue is at an all-time high. Rangan noted that businesses need to diversify the distribution channels they use to connect with customers. 

Building meaningful connections and growing a community are considered critical as it regards cultivating customer loyalty. 

“You need to meet your customers where they are,” Rangan told attendees. 

I tweeted a number of interesting tidbits during the conference on our Twitter account. I’ll be including some of those tweets in this series of blog posts (if you’d like to read more, be sure to follow us at 

After the session, we decided to grab lunch at the “Lawn on D” food truck area outside the convention center. We weren’t terribly hungry at that point (the breakfast sandwiches we’d had were pretty filling), but thought it best to eat while we had time.  

Bridget and I chose to grab food at The Dining Car food truck. I had the Buttermilk Fried Chicken Sandwich with chips:

Bridge had the Honey Truffle Goat Cheese Sandwich (the vegetarian offering featured marinated goat cheese, wildflower honey, and truffle oil with greens and vinaigrette on a ciabatta roll): 

Jolene joined us for lunch soon thereafter. It was nice to get to eat with her at the conference on this trip (since we didn’t have an opportunity to do that in 2019). She sat with us at one of the picnic tables. 

Jolene had the Caprese Sandwich from the Pennypackers food truck: 

And Jason (who did not dine with us) had the Shrimp Po-Boy sandwich from the Revelry food truck: 

After lunch, Bridget and I headed back to the venue’s Main Stage to hear author/speaker/entrepreneur Marcus Sheridan’s presentation titled “What's Next: The ‘Seller Free Economy’ — And the Future of Sales and Marketing.”

We attended a session with Sheridan in 2019 and also watched his presentations at the past two digital INBOUND conferences. He is an energetic and enthusiastic speaker with terrific tips. 

“Thirty-three percent of all buyers say they’d prefer to have a ‘seller free’ sales experience,” Sheridan told attendees. For millennial consumers, that number is 44 percent. 

The buyer is in control — and likes to be in control — and marketers need to keep this in mind going forward. 

“Platforms come and go,” Sheridan said. “Businesses need to build on principles that last.”

Sheridan also used “Choose Your Own Adventure” books in his presentation (to demonstrate that consumers like to feel in control of purchasing decisions). As a child of the 1970s and 80s, I enjoyed the nod to one of the fun book series of my youth!

We would have loved listen to Sheridan talk longer, but were glad to at least have the opportunity to hear him speak (even if it was in a 30-minute slot). 

The next session featured another of our favorite speakers from 2019 — Outcome Media CEO Jay Schwedelson. 

Schwedelson’s expertise is in the area of email subject lines. Like Sheridan, Schwedelson is an enthusiastic speaker who gives attendees lots of actionable tips in his presentations. 

This particular session — titled “Email Marketing Tips: Do This, Not That” — was on the Founders Stage (one of a number of sessions on stages on the exhibition floor — something new that the conference organizers tried this year). 

“The easiest hack in email is to not send out messages on the hour,” Schwedelson told attendees. 

Schwedelson offered a number of useful tips, including the fact that animated GIFs are “killing it” in email today (so you might consider creating them for your email campaigns): 

Overall, it was a terrific session, but (like Sheridan’s presentation) we would have enjoyed hearing more from Schwedelson. 

We then headed back to the Main Stage for a discussion featuring HubSpot Executive Chairperson Brian Halligan. 

Halligan talked about leadership lessons he learned during his tenure building HubSpot. 

He talked about how the company (during its formative years) targeted small and medium-sized businesses with their software products. Investors didn’t like the strategy at the time, but Halligan bet on the notion that “success was more about the width of your brain than the width of your wallet.”

“Whenever the world is zigging, I like to zag,” Halligan said. 

(He also told a fascinating story about meeting Steve Jobs for the first time...)

The final speaker of the day was entrepreneur Emma Grede, Co-Founder and CEO of Good American (a clothing company built on body acceptance and inclusivity). The session — titled “Mapping Out the Moonshot” — focused on Grede’s business journey. 

Bridget and I were familiar with Grede from her guest appearances on the ABC series “Shark Tank” (one of our favorite shows).  

Grede considers herself a serial entrepreneur these days. She discussed her business philosophy and the importance of diversity in hiring. She believes diversity is a superpower. 

“I wake up every day thinking about my customer,” she said. “Every day. I'm obsessed.”

She has built a reputation for understanding where brands and entertainment collide — and the unique opportunity that provides entrepreneurs. 

After the session concluded, there was a reception in the exhibition hall featuring drink stands and mixed-nut trays. Jolene (who is not a fan of sparkling water) described this alcoholic seltzer as tasting like “cough syrup”: 

We went back to our hotel for a bit before heading out to explore Boston.  

I should add that I had slept horribly the night before. There is always an adjustment period when I am on the road, and I didn’t take any Benadryl (which is the same active ingredient as most of the over-the-counter sleep aids) before bed on our first night (something I would rectify for the rest of the trip). 

As a result, I had been up since 4:30 a.m. — I was tired and could have used a nap. But I figured I’d rest when I returned to Omaha, so I kept myself going...

We planned to head north, into more of the touristy areas of Boston (as we had on our 2019 trip). That meant traversing the bus and rail system to get to our destination (Bridget loves mass transit, so she was excited at the prospect). 

I kept seeing these Hippo Insurance Services signs and video ads in the various train terminals we went through. I started collecting hippos as a kid, and love the graphic design this company utilizes in its marketing: 

After departing the underground rail, we looked around the charming Boston Public Market on the way to get dinner. 

The market featured lots of artisan-built knick knacks, including these wooden bowls: 

There were also these unique lawn chairs (that look like the love child of an Adirondack chair and a wheelbarrow): 

After perusing the market, we walked up Hanover St. looking for someplace to eat. The famous Mike’s Pastry was on our path, but we opted not to stuff ourselves with cream puffs, cannolis, and sugary treats (well...not until later!). 

We spotted an Italian restaurant as we walked along — Carmelina's North End — that seemed like it would suit our culinary needs (one of many Italian restaurants along our route). 

One of the interesting aspects of dinner was our server, Brooke. Brooke informed us that she was familiar with Nebraska because she had done an art residency (in 2021) at the University of Nebraska-Lincoln. 

She said, “I liked Nebraska. It’s like going back to the 90s.”

When you live in a Great Plains state, you get used to those sorts of comments from people who live on the coasts (“flyover country” and all of that). That said, the way she worded it was pretty funny. 

The garlic rolls Brooke brought out to start dinner were amazing (honestly, I could have eaten four — or more — myself). 

Bridget ordered the Risotto Milanese as an appetizer for the table (as far as risotto goes, I thought it was good): 

For diner, Jason ordered the Carbonara: 

Jolene had the Sunday Macaroni: 

I opted for the Bronx Tale, which featured meatballs, sausage, tomato sauce, and rigatoni (my dish was very similar to Jolene’s, minus the beef rib and whipped ricotta cheese): 

Bridget had the Gnocchi al Forno: 

Jason and Jolene swapped dishes during dinner (it seemed like a smart idea) to sample each dish. Bridget and I did not (although, I did have a bite of her main course). I thought the food was tasty and would rate it as a solid Italian meal. 

I ate about half of my dish — the rigatoni was really filling. I also knew it would be a long trek back to the hotel, and didn’t want to have any gastrointestinal regrets along the way. 

We had a debate about Bridget’s fancy Pellegrino bottled water during dinner. Jolene wondered if it tasted like the glasses of tap water we had at the table. 

In my “food-coma-lack-of-sleep” state, I thought it went down “smoother” than the tap water, but that could have been my imagination. πŸ˜‰ 

After dinner, we walked across the street to Mike’s Pastry. I opted to watch through the window while my companions stood in line (I am holding the aforementioned bottle of “smooth” water in this picture): 

The people standing next to me in the picture made this joke: “If you have a cannoli in New Orleans, is it called a ‘canNOLA’?” (NOLA meaning New Orleans, Louisiana). 

After I stopped ::rolling my eyes:: I went inside to join the others (to avoid any additional Wednesday night humor). 

Bridget and I bought two cream puffs, an eclair (for me), and a vanilla cupcake (for her) at Mike’s Pastry. 

Jason and Jolene got a cookie and a cannoli. I know the cannoli was for Jason, I don’t know if he also had the cookie. Regardless, I admire their discipline at the bakery (which we obviously did not have). 

Pastries secured, we headed back to the Seaport District and our hotel. It was a pretty packed Wednesday — a day full of food, fun, and education. 

Days like this are what make the trip to INBOUND so enjoyable. And we were excited to see what Thursday had in store for our group! 

The INBOUND 2022 Trip Series: 

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