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The Ross Simmonds Show

12 Oct 2026 · 18m · 6 chapters

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RSS 74: The Transformative Power of Events in Your Career

In short

How in-person career events create long-term growth through connections, trust, and better problem-solving; includes advice on differentiating from AI-written content and how to attend events to add value.

Guest backgrounds

No guests are interviewed in this episode. The host references prior guests/people: Dave Gerhart (mentioned for a past episode about Unbound/Drive prep) and “Laura Anderson” (promotes her podcast Seven Day Weekend).

Key claims

AI outputs are useless without your business data; events change career trajectories even if benefits aren’t immediate; the best conferences blend high-quality content with practitioners and connection-building; attendees should add value in conversations and follow up (e.g., voice notes/AI-assisted reminders).

Notable examples

HubSpot’s Unbound (formerly Inbound) and Exit 5’s Drive in Vermont; a ~50-person workshop on AEO/GEO/LLMSEO leading to ~30 follow-up emails; a six-years-later email from a publicly traded company’s AEO/GEO head met at a conference; announcement of Citation Conference in Toronto (May).

Written by AI. May contain mistakes.

Chapters

2:47

The Impact of In-Person Events

Discover how attending events can lead to unexpected opportunities.

“No matter if you look at the connections that you have had in the past, or you look at some of the most successful people that you know, it's very likely that they got there through connections.”
9:26

Lessons from Recent Events

Understand how insights gained from events can alter your perspective.

“Listen to the seven day weekend wherever you get your podcasts.”
14:01

The Long-Term Value of Networking at Events

Learn how relationships formed at events can lead to unexpected opportunities.

“asking for a follow-up and have a call about how they can improve some of the things going on.”
15:02

Strategies for Adding Value at Events

Discover effective strategies to contribute and stand out during events.

“Six years later, conferences and connections don't always pay immediate dividends, but they will pay dividends in the future if you go into the events with one intention, add value.”
16:18

Announcement of the Citation Conference

Get exciting details about the upcoming Citation Conference in Toronto.

“is that if you go into events with the intention of adding more value to those who are in attendance than they even thought that they would get if they didn't go, you'll be able to win.”
17:43

Closing Thoughts on the Importance of Events

Reflect on the significance of attending events and ongoing engagement.

“It's going to be a blend of both of what I saw from Unbound and what I saw from Exit 5's Drive.”
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Transcript

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0:03Does your experience with AI sound a little something like this? You've been prompting for 20 minutes. The output is polished, confident, and completely useless. That's what happens when AI doesn't know anything about your business. HubSpot's AI works with your actual customer data, every interaction, every signal your team has generated over time. So instead of prompting and hoping, you ask once and you ship it. Check out HubSpot.com, the agentic customer platform for growing businesses.

0:34Over the years, I think I've averaged probably anywhere from$20 ,000 to$30 ,000 on travel costs, accommodations, mileage, food, etc. to go to conferences. Most recently, I got back from Unbound and Drive. Unbound was put on by HubSpot. It's the new version of the event formerly known as Inbound. And Drive is put on by the folks at Exit 5. You should check out my episode with Dave Gerhart where we talked about the prep and the lead up to that specific event that was held in Vermont. Beautiful place, by the way. These events played a key role in what the next 12 months will bring. and what I don't know today is how these events will translate into something in the future.

1:29What I mean by that is when I look at my career, the investment that I have made either with my time or money to go to events has played a key role in the trajectory of foundation, in the trajectory of my career, in some of the deepest and strongest friendships and relationships that I have both personally and professionally. And in the moment, you don't oftentimes know that it's happening. I believe that one of the most effective ways to increase your ability to get lucky in business is to increase the likelihood of you making connections, Building trust, building rapport. In this episode, I'm going to talk about the role that events have played in my career in driving growth, how I'm thinking about events going into 2027, and an announcement that I hope you will actually take into consideration as something that you might tap into in the future.

2:30Folks, I think events can change your life. And in this episode, I'm going to give you the playbook on how I was able to use events to change mine with the hope that they will influence yours. If you're always into playing the long game, you're in the right place. Welcome to The Ross Simmons Show.

3:03Connections run the world. No matter if you look at the connections that you have had in the past, or you look at some of the most successful people that you know, it's very likely that they got there through connections. Someone, whether it was a professor, a colleague, a peer, a mentor, or someone that they worked with, a business partner, a co-founder, a manager, a lead, whatever it was, saw something in them, helped them, supported them, encouraged them, guided them, coached them, nurtured them, taught them. We all become who we are through our network. And don't get me wrong, I recognize that not everyone's network is created equally.

3:45When I first got started in business, I didn't have any aunts or uncles who could give me an internship in the wonderful world of software or tech or business. I had to try to open up new doors. And for me, the connections came through the internet. I used the internet to create a bunch of content, answering questions on X when anyone would tweet out something about social media, engaging in group chats and weekly chats on a regular basis that were happening on channels like Twitter. I would go into forums and communities and respond intentionally with as much value as I possibly could give to different people asking questions about marketing and try my best pre-AI to actually give my perspective and my take.

4:28Now today, don't get me wrong, a lot of people are doing this, but they're control C and control V-ing perspectives from ChatGPT. They're not their own perspective, it's not their own opinions, and it's not their own beliefs, and as such, I believe it's harder than ever for us to stand out. The blueprint that I used to go online and actually contribute to these communities doesn't actually work as well as it used to. Why? Because people think and see that a lot of people are replying with nothing more than LLM copypasta. so to speak. What you really need to embrace in today's day and age is wondering how can you differentiate?

5:04How can you make it so obvious that an AI didn't write your comment? How can you make it so clear that this was actually your perspective, your brain, and your eyes viewed the content and actually wrote the content yourself? How do you do that? There's a few different ways like you can make it more personal, you can speak to your own experience, you can make sure that you are not using the perfect writing and style and grammar and format that an LLM would use. You're making sure that you're not using the AI-isms like in the ever-evolving world of. You might not be starting your sentences with the same period after three words.

5:39You're not talking about layers. You're just getting to the point. We all see the AI comments, but what I love is that in person, No one can bring the AI. Sure, there's metaglasses. These aren't them, but people can bring metaglasses and potentially in the future, they'll be able to cheat. But for now, when you see someone, there's no AI filter. There's no AI cheat sheet that is coaching them and guiding them on how to manage that interaction. So you start to get the real human side of people. You discuss things that matter to you. You discuss your problems. You discuss challenges. You discuss work and life.

6:21You discuss things that you want to see change in an industry. You discuss applications that you're building, products that you're working on, features that you've created, and maybe even give someone a demo of an agent that you created. That is the power of in-person. When I went to drive, my light bulbs went off. and they went off as a reminder, a reminder of what a cool industry we work in is. As marketers, we're kind of on the cutting edge of a lot of shifts that are happening with culture. Buyers are changing the way in which they buy. Businesses are changing the way in which they work. And as marketers, because technology is a key part of our role, we get a front row seat.

7:10I saw HubSpot announce some features and things inside of Breeze, inside of their CRM with auto updates that absolutely blew my mind. That made me so grateful to be able to say not only that I was there, but that I'm in an industry where this type of shift is happening. Then I go to Vermont for Exit 5's event with a bunch of B2B marketers geeking out about the thing that we all can come together and geek out about, which is B2B marketing, talking to other SaaS marketers about how they're thinking about Reddit, how they're thinking about SEO, how they're thinking about go-to-market direct mail, how they're thinking about partnerships and generating leads on the back of remarketing campaigns and inbound efforts and outbound and what's working and what's not.

7:59Earlier on in this episode, I talked about how events create connections that you don't even know in the moment provide opportunities in the future. From HubSpot's Unbound to Exa5's Drive, I have confidence in two key things that I'll leave with and that I've left with. Do I know them right now what they are? No, but I can say with confidence that there's two things that I'm going to leave with.

8:29Seven Day Weekend is brought to you by the HubSpot Podcast Network, the audio destination for business professionals. Self-proclaimed anti-workaholic Laura Anderson brings together this podcast and it's something that you really should check out. It's a podcast where people are going to learn the ins and outs of business, finance, side hustle, and more. In this podcast, Laura brings to life some of the brightest guests who have started their own business from the comfort of their own home to create businesses that generate anywhere from 10 to 20 to 30k a month. This is a podcast that anybody who doesn't want to get caught up in the corporate race, the rat race, if you will, should definitely check out.

9:06If you're maybe thinking about how you can use a side hustle to escape at your nine to five, this podcast might be for you. Laura brings in guests and also delivers authentic and real conversations into your earphones based off of lived experience. If you want to live your own seven day weekend, then this is a podcast that you won't want to miss. Listen to the seven day weekend wherever you get your podcasts.

9:34from the sessions at both of these events, I know that the way in which I think will be forever altered, or it will be temporarily altered to see things differently. A problem's going to come across my desk. A challenge's going to come across my desk. And because I attended these events and heard other professionals, other experts, other leaders talk about their approach to dealing with these things, the way in which I pattern match those problems is going to fundamentally be different than it would have if I didn't go. That's the magic of events. Someone is going to write me an email and they're going to ask me a question about CRO.

10:19They're going to ask me a question about landing pages. They might even ask me about whether or not we need a certain amount of time to do data cleaning of a CRM. And because I attended these events, I have solutions and ideas that might be more efficient, more effective, and able to help guide them down a path that is different than the one I would have given and the recommendation I would have provided three months ago. That's the power of events. Now, a lot of events don't prioritize the importance of great content. They prioritize instead the importance of having a big name on the stage. Now, I'm not going to say which events, but I've been at a lot of them, where they put these fancy names on stages, these people speak, and you get absolutely nothing valuable from them.

11:13They say things like, synergy is the future. The key to search is understanding your buyers. The key to marketing is recognizing that the future is in your hands. They say a whole bunch of plateaus without saying anything at all. This happens every single month. Conferences are held where someone gets on stage and because they're a former politician, athlete, celebrity, they get the seat as a keynote who delivers no value. There's nothing worse. Now, don't get me wrong, they sell tickets. There's a role for it to play. But for most brands, the key that I would say for them is to take a page out of HubSpot's book.

12:03You get brilliant people on some of the main stages. You get brilliant people in the industry on main stages. And you also have the keynotes who can speak to experience of media, who have written books, who have done ridiculously insightful, inspiring things. But you have a blend of that with your content. I love that model. Exit 5's model was very different. They brought in practitioners. They brought in people who were actually doing the work. CMOs, VPs, directors of marketing, people who were hands-on keyboards, executing projects with the goal of hitting targets and metrics. It was a great event.

12:47absolutely amazing event. And the amount of material that I left with was huge. But what was most impressive was the amount of connections. Because they operated this event with that second thing in mind that you leave a good conference with. And that is connections. Connections will fundamentally change your career. Insights can fundamentally change your career. And at exit five, there was a lot of room and opportunities to build connections. I ran a workshop. It was about AEO, GEO, LLMSEO, AEO, EIEIO. It was about that concept, right? That joke is never getting old. I held this session with, I think, about 50 people.

13:35And what that led to was 50 people having an opportunity to hear my perspective, but also my opportunity to hear from 50 people about their individual situation and walk through how AEO, GEO, et cetera, could be applied to their space. Since that session, I think I've had about 30 emails from people who were in that workshop talking about how much value they got out of it, asking for a follow-up and have a call about how they can improve some of the things going on. And I can say with confidence that out of that workshop, we're going to drive value monetarily for foundation, but we're also going to unlock relationships and potential opportunities that I don't even know about yet.

14:21Just yesterday, I got an email from a big brand, publicly traded, worth billions of dollars. It was their head of AEO and GEO. I met this individual six years ago at a conference. We were at a conference. We were talking about the situation in their business at a different company. We had a 40-minute chat. Didn't really stay in touch. We added each other on LinkedIn. I assume they may have watched a few YouTube videos. They might even listen to this podcast. If that's you, what's up? They heard and continued to follow the journey of our story, and then they reach out. Six years later, conferences and connections don't always pay immediate dividends, but they will pay dividends in the future if you go into the events with one intention, add value.

15:16Try to show up and add as much value possible. What does that mean? It means different things depending on who you are at the event. If you're a speaker, you better deliver on stage. If you're an attendee, in every side conversation that you have with a peer, try to be the person that they remember as the person who helped them solve a certain problem. One of my tips that I've been giving for years is after you meet someone, pull out your phone and record a quick voice note describing what you discussed and who you talked to. AI makes this even easier. Go to an LLM and say, hey, you're going to owe this person, this deliverable, this project, this link, a book, or a recommendation on a certain thing based off of the combo that you had on day two at this event.

16:01You do these things and the relationships just get strong, folks. I used to take pictures of business cards and then email them to myself and write an email describing who I met and what I talked about with them. So I wouldn't forget it. Everyone's going to play a different game. But the one thing that I will say with confidence is that if you go into events with the intention of adding more value to those who are in attendance than they even thought that they would get if they didn't go, you'll be able to win. Don't be the negative person at these events. Be the person that people want to remember for bringing good vibes and good energy.

16:33And with that, I'm excited. I'm excited to announce that come May next year, Foundation is going to be running our inaugural of first event. It's called Citation Conference. Citation Conference is going to be held in May. The link is going to be in the show notes. It's going to be held in Toronto, Canada. I would love for some of the listeners of The Ross Simmons Show to show up, to join. I'll probably be doing an onsite live recording of a few of these episodes, and I would love for you to be in attendance. I'd love to see you at the event and live up to the promise that I've made here today, which is my simple goal whenever I walk into a conference, to give people as much value as I humanly possibly can, to be selfless with the resources, the data, and the insights that I can give to this industry.

17:24because if I do, then it's going to force me to level up again. And my hope is that at Citation Conference, I not only see you there, but I also can add as much value to you as possible. Check it out, citationconf.com. Our team is thrilled to be launching this and are excited to host it. It's going to be a blend of both of what I saw from Unbound and what I saw from Exit 5's Drive. I'm inspired by some of the greatest events that I've attended over the years, and I'm hoping that I can incorporate it into this one. We're going to be working diligently to attract the right people, to get the right people on the door.

18:01And if you're interested, go request a seat. We'd love to see your name there and we'd love to potentially have you there on the ground. So with all that said, I hope you enjoyed this episode about events. I hope to see you on the road at one of the many events that I will be in attendance to over the next 12 months. And if not, hey, I'll see you on the internet.

From the publisher

The internet is flooded with AI-generated content right now, and that makes real human connection worth more than ever. In this episode of The Ross Simmonds Show, I break down the value I’ve seen from showing up at in-person events and how strategic networking and learning have shaped my own career. I share how I approach getting ROI from a conference and why the payoff from those rooms keeps showing up for years afterward.

Key Takeaways and Insights:

1. The Unseen ROI of Conferences

- I treat events as a long-term investment in my career, my relationships, and the growth of the business.

- Some of the biggest opportunities I’ve had came years after the first conversation.

- If you want to get luckier in business, put yourself in more rooms where genuine connection can happen.

2. Building Your Network from Scratch

- When I started out with no industry connections, online forums and social media chats were how I built my network.

- Standing out online is much harder today because feeds are full of low-value AI comments, what I call “LLM copypasta.”

- The way to cut through is to bring your own experience and point of view into every online interaction.

3. The Power of In-Person Connection

- In-person events get you out of the digital noise and into real, unfiltered conversations.

- Talking face to face about challenges, goals, and ideas builds relationships people actually remember.

- I’ve found the trust you build in person is something you can’t replicate over a screen.

4. How Events Reshape Your Thinking

- Every good conference I attend gives me new mental models for solving problems.

- Hearing how other experts think changes the way I approach challenges in my own work.

- I walk out with faster, sharper solutions than I had when I walked in.

5. What Separates Great Events from Bad Ones

- The worst events I’ve been to lean on big-name “celebrity” speakers who give generic platitudes and nothing you can use.

- The best ones mix inspiring keynotes with practitioners who are in the trenches doing the work every day.

- I look for events that build in both structured and unstructured time to network.

6. The Ultimate Event Strategy: Add Value

- My number one goal at any event is to add as much value as I can to every interaction.

- If I’m speaking, I want to deliver an exceptional presentation. If I’m attending, I’m looking for ways to help people with their problems.

- I want people to leave remembering me as someone who brought good energy and useful advice.

Resources & Tools:

🔗 Foundation’s Citation Conference - https://citationconference.com/

🔗 ExitFive’s DRIVE 2027 - https://exitfive.com/drive-2027/

🔗 HubSpot’s UNBOUND 2027 - https://unbound.hubspot.com/

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