Ryan Holmes

Ryan Holmes

Entrepreneur and angel investor. CEO & Founder of Hootsuite

THIS CHAT HAPPENED ON November 03, 2015

Discussion

Ryan Holmes
Ryan Holmes@invoker · ceo
Hey, I’m Ryan, the CEO of Hootsuite, a social media management company I founded in 2008—which now has over 12 million global users, including 800 of the Fortune 1000 companies. I’m also an angel investor, startup advisor and co-founder of The Next Big Thing, a non-profit foundation that supports young entrepreneurs. Ask me anything about social media, entrepreneurship, tech, marketing and—if you must—my beard.
Sydney Liu
Sydney Liu@sydney_liu_sl · Co-Founder of Commaful.com
Hey Ryan! Thanks so much for doing this AMA. Huge fan of the product. Have been using it for a number of accounts and have recommended it to many friends. How did you grow Hootsuite to scale? Since people us it to promote their own content, doesn't seem to lend itself to viral loops. Or was it more that people love the product so much that they share it with other people who may need it? (Like I did). Was there anything you did to optimize for this? Thanks, Sydney
Ryan Holmes
Ryan Holmes@invoker · ceo
@sydney_liu_sl Hi Sydney, Great question. A few viral loops a few top of mind... 1) We built a passionate user base (http://signup.hootsuite.com/amba... ), and those people became huge evangelists. 2) Early branding through url (ow.ly, ht.ly) 3) Tweet the love - when we do product launches we ask excited users to share if they are excited Hope that helps
JJ Tang
JJ Tang@jjrichardtang · Product @IBMCloud 🚢
Hey Ryan :) If you could time travel back to day one of Hootsuite and have 15min with your former self to communicate any lessons you've acquired with the intention of saving yourself mistakes and heart ache, what would you tell yourself? Bonus quick fire questions: a) Favourite emoji and why? 🤓 b) Top 3 favourite disruptive Canadian companies
Ryan Holmes
Ryan Holmes@invoker · ceo
@jjrichardtang You've probably heard before, but hire slow, fire fast. You really need to get A players onboard and it's tough when you're scaling fast. Have the hard conversations asap. Bonus - a/ Fav emoji... poo http://www.fastcompany.com/30378... b/ Shopify, Slack, and modesty forbids re #3.
JJ Tang
JJ Tang@jjrichardtang · Product @IBMCloud 🚢
@invoker @jjrichardtang I completely agree with you. It's very interesting because my conversation with Walker Williams of Teespring he said the biggest lesson he learned was the cost of hiring the wrong people. Great to see a parallel drawn here. Love the background story behind the poo emoji...not sure if I should have opened that webpage up during my lecture though! Thanks for doing an AMA!
Emily Hodgins@ems_hodge · Operations @ Product Hunt
What one piece of advice would you give to someone just starting out a new business right now?
Ryan Holmes
Ryan Holmes@invoker · ceo
@ems_hodge Find a big wave. It's simple, but to use a surfing analogy, you can be a great surfer (entrepreneur), with no wave and you won't get anywhere. Given a great wave, even average surfers can get carried along.
Jake Crump
Jake Crump@jakecrump · Community Team with Product Hunt
What does a regular work day look like for you?
Ryan Holmes
Ryan Holmes@invoker · ceo
@jakecrump 1/ Wake up 2/ Check @hootsuite mentions, @invoker mentions, facebook, email to see if there are any pressing fires 3/ Drink hot honey & lemon on 4/ Walk to work 5/ Do yoga sometimes 6/ Team meetings, Email, Board, Product reviews, Marketing reviews (P&M are where I spend a lot of time). 7/ Sometimes lunch workout 8/ More of 6 9/ Head on home 10/ If i didn't work out at lunch, go for a run (exercise kills my stress and helps me work on hard problems) 11/ Eat, catch up with friends. Shit this sounds kinda boring, but I kind of love my average days.
Kamil
Kamil@kamilszybalski · Growth Entrepreneur. Was @Hootsuitelabs
Hey Ryan, what are you currently reading?
Ryan Holmes
Ryan Holmes@invoker · ceo
@kamilszybalski Favorite books collection: Ender’s Game: Beyond just great storytelling, Ender’s Game is also a useful book for leadership inspiration. It explores larger themes of power, intelligence, free will and perseverance. Born to Run: Born to Run is the true story of author Christopher McDougall, who sets off to find a tribe of the world’s greatest distance runners and learn their secrets. As thought-provoking as Born to Run is, it’s also inspirational. It shows us that we are more than we have been taught to believe. Creativity Inc.: Co-written by Ed Catmull (the president of Walt Disney and Pixar Animation Studios), it’s full of brilliant business lessons on how to build creative culture that benefits organizations. The Long Walk: The Chicago Tribune called The Long Walk “one of the most amazing, heroic stories of this or any other time,” and I highly agree. Delivering Happiness: Written by Tony Hsieh (the guy who transformed a virtually unknown shoe retailer called Zappos into a $1.2 billion company), Delivering Happiness is full of advice, anecdotes and interesting business ideas. Getting Real (37 Signals): This quick read is essentially a business manual about how to build great web products—that touches on things like design, programming, and marketing. An Astronaut's Guide to Life on Earth: I recommend anyone who dreams big and who strives to stay true to themselves to read this book. Where the Wild Things Are: This was my favorite book as a kid but even now, I can still relate to the main character Max and his rebellious spirit. I think it’s a great reminder to stay imaginative. Abundance: The Future is Better Than You Think: This is a great book, which suggests the world as we know it today is the best it’s been, but nobody realizes it. It’s an eye-opening read and worth checking out.
Ryan Holmes
Ryan Holmes@invoker · ceo
@invoker @kamilszybalski I copied that from a linkedin post btw. I'm fast, but not that fast.
Mounir Ahmina
Mounir Ahmina@0xmounir
Hi Ryan. When you think about Hootsuite's early days, what action you think about it as "If I didn't did that back then... Hootsuite wouldn't be successful today"?
Ryan Holmes
Ryan Holmes@invoker · ceo
@m0un1r_ so many decisions... - we had a lot of investment interest, and had we taken some of those, we would have been in a tough spot - we declined acquisition which would have been game over - if we focused on monetization vs product too early i think it would have caused issues - if we invested in advertising vs building product
Harry Stebbings
Harry Stebbings@harrystebbings · Podcast Host @ The Twenty Minute VC
Hi @invoker thanks so much for joining us today. This is a bold question and I do not mean to be rude. I am a Buffer customer, why should I choose Hootsuite over Buffer, what makes you the best in the industry? I am so sorry for the bluntness not meant to be rude, would love to hear your thoughts.
Ryan Holmes
Ryan Holmes@invoker · ceo
@harrystebbings Fair question. We've got to earn your business! We offer all of the same functionality such as scheduling, auto-queueing etc, but also extend much further with engagement (listening/response), customer support etc. If you're looking for really simple functionality, check out http://www.hootlet.com/ and our suggestions app (https://hootsuite.com/products/m...)
Kate
Kate@katesegrin · Head of Social @ GitHub
What are some of the most "magical" or inspirational experiences you've had working with young entrepreneurs?
Ryan Holmes
Ryan Holmes@invoker · ceo
@katesegrin Since setting up wearetnbt.com I've had the honour of working with some of the most inspiring Canadian entrepreneurs. I'm constantly amazed with how much more sophisticated they are at 17-21 than I was at their age. Biggest inspiration out of last cohort, shareshed.com, funded and moving fast. Dan is going to have an amazing career.
Lejla Bajgoric
Lejla Bajgoric@lejlahunts · Intern, Product Hunt
Hi Ryan! What's the "next big thing," if you could make a prediction? Or if that's too broad -- in what sector will the next big disruptive startup take place? Transportation? Communication? Thanks!
Ryan Holmes
Ryan Holmes@invoker · ceo
@lejlahunts HUGE thing would be energy disruption (plug for these Vancouver guys... http://www.generalfusion.com/). Transportation (Tesla - Check), Communication (FB, TW, Slack, Hootsuite - Check). Basically I look at star trek and it's all happening... faster than we think.
Jake Crump
Jake Crump@jakecrump · Community Team with Product Hunt
What's something that you've changed your mind about in the last year?
Ryan Holmes
Ryan Holmes@invoker · ceo
@jakecrump I think the dress is actually Gold & White.
Cory Crowther
Cory Crowther@graphikmovement · Owner / Ottono.co
@invoker What stage in the startup process should you think about patenting intellectual property, if at all?
Ryan Holmes
Ryan Holmes@invoker · ceo
@graphikmovement patents in saas software world are a bit of a philosophical debate. For most scrappy startups it burns a lot of cycles and can be distracting. If you're self or limited seed funded I'd generally say skip it. All this being said, I wish we'd patented a few more early innovations we invented like social media scheduling, but who knows what would have fallen by the wayside.
Ryan Holmes
Ryan Holmes@invoker · ceo
Thanks everyone, this was super fun. I've got to bounce right now, but will try to get back to pick off a few other questions when I've got a minute. Keep hustling and blow shit up!
Wen Wilson
Wen Wilson@acreerph · CEO & FOUNDER , HEALTHCITE
@invoker . Did you bootstrap for a number of years before seeking VC or angel investment? Did you decide early on to make Hootsuite a freemium service?
Ryan Holmes
Ryan Holmes@invoker · ceo
@acreerph Yes, we bootstrapped for a year before VC. We ran for a year as freemium for 2 years when we finally launched out paid plans. We had 1m users at that point and were cashflow positive 2 months later.
Emily Hodgins@ems_hodge · Operations @ Product Hunt
Hi Ryan thanks so much for being here today! During your career to date what has been your a) most challenging moment and how did you overcome it? b) proudest moment and why c) most surprising moment? Thanks!
Jourdan Bul-lalayao
Jourdan Bul-lalayao@jourdanb21 · Co-Founder & CTO, Jobox
Hey Ryan!! Thanks for doing this AMA with us on Product Hunt! My question is intentionally vague as I'd love for you to answer it based on your interpretation of the question :). If you had only one tip to share with entrepreneurs on how to build a successful startup, what is your absolute #1 tip?
Kate
Kate@katesegrin · Head of Social @ GitHub
What kind of yoga do you practice, and have you ever had an "aha" moment on your mat (whether it's finally getting into a pose or other revelations)?
Ryan Holmes
Ryan Holmes@invoker · ceo
@katesegrin Hatha most frequently, but also some Vinyasa flow and love hot settings. Love variety, and yes, I have a TON of aha moments.
Kate
Kate@katesegrin · Head of Social @ GitHub
@invoker what's the most recent "aha" been?
Tigran Hakobyan
Tigran Hakobyan@tigranhakobian · Entrepreneur, Co-founder/CMO @ inapptics
Hi Ryan, thanks for joining us at Product Hunt Live! What's your advice for young entrepreneurs: bootstrap or raise? And why?
Tigran Hakobyan
Tigran Hakobyan@tigranhakobian · Entrepreneur, Co-founder/CMO @ inapptics
Hey Ryan, I'm a big fan of Hootsuite and have been using it for different projects. How did you get your first 1K users? We are going to launch our beta product soon (a mobile app analytics tool) and it'd be great to get your advice.
Ryan Holmes
Ryan Holmes@invoker · ceo
@tigranhakobian Focus on product, product, product. Once we had that built out, first 1k came in through friends and friends referring friends. If your product solves a big need, this should automagically happen. Having a freemium model also helps, but if your product is shit, even that won't help.
JJ
JJ@outdreamer · Web Developer/Writer/Idea-generator
What is a strategy you use when the ambitions of your beard conflict with those of your brain and/or when a beard gets inappropriately mouthy? What is a time when your beard threatened to outshine your outfit & did you reign it in by example, fear, or love?