5 lessons learnt throwing an event
And why you should do events as well.
Last weekend, we ran Underdog Live: E-Com Edition, welcomg a group of 30+ participants who joined in person and online (you can still get a pass to recordings here)
The thing about events is it isn’t just another “conference” or “workshop”. It’s a marketing strategy disguised as one. Let me explain.
1 - Power of physical presence
Nothing beats meeting a living, breathing customer in person. No email, ad or webinar can replicate the way people connect in real life.
The simple conversations and handshake you have in real life will build more trust than 6 months of posting online.
The lesson: Events aren't just a money-making tool. They shorten the trust timeline. Every company at some point will have to touch their audience physically.
2 - Hidden ROI
Everyone assumes we make money from events. They look at the number of people in photos, and make an assumption that we made a lot of money.
Events are actually expensive.
Nevermind the cost of setting one up, people forget the resources (staff costs, time, etc.) to planning and making one happen.
The ROI of events will always, almost come from opportunities on the side:
- Connecting with someone who needs what you offer.
- People who sees you running an event and decides to reach out.
- Side deals
3 - People don't appreciate "free"
Tough stance I know.
Yes, that there are great, big-hearted people who appreciates free. And I'd love to dream of a world powered by "free". But yet, the market decides.
There will always be people who take "free" for granted. Run a free event, and you'll see an average of 50% showing up. Run a paid event, and you'll see attendance at 95%.
Nothing wrong with giving things for free or charging for it. Just know that you might want to change your strategy depending on the situation.
4 - Hit when rod is hot
It's tough to communicate excitement an anticipation online. The energy of watching a concert in real life, versus watching it on YouTube on your 6.5" smartphone is different.
One of the thing that we're trying to do more intently is to collect customer testimonials in written and video format.
The best time to collect a testimonial? When the customer is in the excitement and feeling that energy itself. We sent out surveys late (should have been on the spot) and forgot to record video interviews on the event itself.
Lesson: Whether proposals, testimonials, or asking for the sale. Always hit when rod is hot.
5 - The irony of digitalization
While digitalization has made us more connected than ever, the irony is that we're more disconnected from each other than ever.
And the weird thing that I've observed is that the more "digitalized" we become, the more we start seeking out in-real-life experiences.
That's the opportunity for you as a business owner. In 2026, I would focus on creating more in-real-life experiences for our audience.
Underdog Live was made possible by INFINITY8
INFINITY8 is one of the most professional co-working and event spaces I've worked with.
From check-in calls to checklists, to making sure our event goes well, I've never came across a co-working space this detailed with a team that works so hard.
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