These videos have made me a better entrepreneur, and I hope they do the same for you.
A lot of keynote speeches and “business talks” are simply bad. They’re self-promoting, self-congratulatory and ultimately self-serving.
But when done well, talks can be incredibly valuable.
They give you an insight—in just a few minutes—into years of hard work and learning that the speaker has done. I love the efficiency of that medium, and make it a point to watch a few videos each week that I think might teach me something.
So today, I’m sharing a few of my recent favorites in the hopes that they’ll be as valuable to you as they were to me…
Note: At the end of this post, you’ll find a special discount for Groove readers to attend what I truly believe is the best, most value-packed software conference of the year.
1) What I Learned in a Decade at Hubspot
HubSpot generated $271M in revenue last year.
The company is ten years old, and co-founder Dharmesh Shah has seen every minute of the long, hard battle the company has fought to get to where it is today.
In this talk, Dharmesh shares some of the biggest mistakes the company made along the way, and what we can learn from them.
Personally, I loved the honest insights on failing to diversify the team early on and how it ultimately hurt the company. It’s something that many startups struggle with (including ours), and I’m glad Dharmesh talked about it.
Beyond the culture challenges, this talk goes into critical assessments of branding and product management that made me think very hard about some of the things we’re doing at Groove.
2) Lessons Learned in 17 Years Building and Exiting a SaaS Company
Gail Goodman is the CEO of Constant Contact, an email marketing juggernaut that went public in 2007 and was later acquired in 2015 for $1.1 billion.
In this talk, Gail breaks down the three stages of a SaaS company’s lifecycle, and shares key insights that helped the company continue to grow where so many others failed (hint: don’t sleep on your customer referral strategy).
Her transparent retelling of when the company knew that it was time to look for an acquirer in a period of stagnant revenue growth—despite other metrics looking healthy—is an important reminder of the dangers that a public company faces.
Gail’s talks are always excellent, and this one is no different. I’ve previously recommended her discussion of The Long, Slow SaaS Ramp of Death, one of my favorite talks on the topic, ever.
3) Here I Go Again. Why My Second Startup is Different.
Groove was the third startup I founded (or co-founded).
And while I’ve never learned more (or faster) than I have in our journey, I took quite a few lessons from my past experiences, and they’ve helped us avoid a lot of mistakes this time around.
I always enjoy hearing how second-time founders are approaching their newest startup differently, while the wins and scars of their past venture are still fresh in their mind.
In this talk, Nick Halstead, formerly the founder of DataSift, discusses “doing it all again” at his newest company, Cognitive Logic.
Nick covers important issues that most first-time founders don’t think about deeply enough, like dilution, careful team-building, and the power—and absolutely non-negotiable necessity—of good storytelling.
And while I don’t necessarily agree 100% with it (I’m lucky to know a few rare gems), I did absolutely love this slide from this talk:
A Special Offer for Groove Readers
The three talks linked in this post are from the Business of Software conference.
It’s one of the few conferences that I know truly delivers huge value consistently.
They don’t have panels, software pitches sponsor presentations or anything like that; just smart people sharing hard-earned advice.
I’m fortunate to know the organizers, and with the event coming up in September, I got them to offer a discount to Groove readers.
I want to make this very clear: this is not a kickback referral link. I/We get nothing if you click on it and buy a ticket.
My only goal here is to offer our readers more value with a discount to what I believe is the best tech conference of the year.
With that out of the way, click here for 20% off of the Business of Software conference, September 18th-20th in Boston. This year’s keynote speaker is Seth Godin.
The link should apply the discount automatically, but if you’re asked for a code, just enter GrooveHQ.
How to Apply This to Your Business
There’s a good chance that you already seen some of these videos.
But I hope that in this list, you’ve found at least one or two new sources of insights that will help you grow your business and become a better entrepreneur.
I’m curious to hear: what are your favorite talks?
Let me know in the comments.
