Rob Smith is the founder of Team Huddle, a new end-to-end AI-powered meeting platform designed to address the universal business problem of ineffective meetings. With 15 years of leadership experience in AI, technology, and marketing firms, Rob understands that people work — and meet — differently across roles and industries.
With his team, Rob is on a mission to put people at the center of meetings by leveraging AI and machine learning to set people up to do their best work and achieve a positive work/life balance. Previously, he founded three other startups and served as interim CxO and advisory roles at a half dozen VC-backed Bay Area startups over the past three years.
What is Team Huddle all about?
The problem that Team Huddle focuses on is a simple fact: most meetings suck. That makes Team Huddle’s goal remarkably simple: Make meetings better. Team Huddle is a new end-to-end AI-powered meeting platform designed to address the universal business problem of ineffective meetings.
Although we’re a meeting company, our focus is not on meetings themselves, but the people attending, you. If we’re successful, we will change company culture to recognize that in order to improve meetings, we need to first understand how people work best.
We’ve started by addressing scheduling because the way solutions are approaching it today isn’t effective. Finding the next available time is a terrible way to plan a meeting. Solutions like Calendly treat your schedule like a car wash or pet groomer: Fill up your calendar to the brim!
Our free initial product ScheduleIQ combines the world’s first ScheduleScore, a credit score for your calendar and work/life balance, and our SmartScheduler. Our human-centric scheduler understands how you work best, and optimizes around your unique work profile. Meet for a living? We’re going to try and give you some breaks in between. Work as a developer or designer? Let’s schedule all your meetings in the morning so you can work uninterrupted in the afternoon. We recognize that every person works differently, so their schedules need to reflect that.
Tell us a little about your background and how you started your company?
While I have a math degree, my experience is entrepreneurship through and through. This is my third startup and fourth company, so it’s not my first rodeo. My first startup was an ad agency/production house out of London, followed by an AI-powered marketing automation startup in San Francisco. For the past four years, I’ve led a small tech and marketing team at RS Consults as a CxO-advisor at a number of Bay Area VC-backed startups in a variety of industries, from medical to marketing to fintech in engagements lasting from one to 18 months.
It’s that wide exposure to a number of industries and company sizes that have helped us become subject matter experts in the meeting space. We’ve been able to validate that meetings are expensive and broken in most companies.
When talking with my other co-founders about being an entrepreneur at heart and wanting to start a new venture, meetings quickly became our primary focus as a space where we could have real impact and change the world in a meaningful way. And here we are about a year later!
What would you say are the top 3 skills needed to be a successful entrepreneur, and why?
- Risk Appetite: Want to build a big company and change the world? Be ready to risk it all; Salary, late-night hours, and sometimes personal relationships. You’ve got to be comfortable with risk to have any chance of hanging in there during the inevitable ups and downs.
- People Skills & Communication: It all boils down to people. Whether it’s hiring and finding the best talent, convincing an investor to sign a term sheet, or motivating your team to keep fighting, if you can’t read people and communicate effectively, it’s going to be an uphill battle.
- Versatility: Entrepreneurs, especially in the early stages, have to be ready to roll up their sleeves and dive into just about anything: IP, product, marketing, financing, accounting, etc. You’ll have help, but in the end, most of the slack will be picked up by you.
- Simplify: Being able to simplify what may seem to be an impossible task into a manageable list of action items is your number one job. You’ll often be working with a small team and have unreasonable deadlines and expectations. KISS philosophy (keep it simple, stupid) is a must.
What are your plans for the future and how do you plan to grow this company?
World domination. All joking aside, our plans probably don’t differ too much from other startups at our stage. It’s not rocket science, but it is hard to do: Listen to the data, learn from our customers and build a product people love.
The difference at Team Huddle, however, is our growth model. Meetings by default are a group activity. We believe at the core that if people love meeting or scheduling meetings using ScheduleIQ, it’ll spread naturally and organically throughout an organization or team. If we do our job right, we’ll have less control over our growth, and our primary job will be keeping up with the needs of our growing base of Huddlers.
How have the pandemic and lockdown affected you or your new business?
We came up with the idea for Team Huddle a few months before COVID-19 shut down planet Earth and forever changed the workplace. It had zero impact on our product and mission. If anything, the pandemic threw fuel on the fire of change needed in the meeting space.
Internally, it was the most difficult process I’ve ever been part of. Dreaming up an entirely new idea, designing and building a first-of-its-kind platform, and raising money without physically seeing another team member or investor was mentally and psychologically challenging. We all suffered in our own way and coped differently too.
Without speaking for the whole team, I am a perpetual nomad, having traveled every month or so for the past 20 years. To keep my sanity, I booked hotel stays next door to my home in Toronto every other week to simulate my “normal.” The first time I saw a co-founder and other human beings after almost a year of isolation was emotional, weird, and reminded me normalcy isn’t that far away.
How do you separate yourself from your competitors?
The meeting space is crowded, but most startups are focused on either making meetings easier to have or set up. We’ve taken a minute and asked ourselves: Why are we meeting in the first place? How could we meet better?
Most meeting software serves the meeting: More meetings, more scheduling, more notes, more, more, more. People feel the busier their schedules are, the more “productive” they appear. Team Huddle’s main mission is to change our view of meetings. We believe meetings are valuable but very expensive. People should be invited to fewer, but highly productive meetings that have a clearly defined purpose.
What were the top three mistakes you made starting your business, and what did you learn from them?
I’m not a huge fan of numbered lists, but I’ll give this a shot:
- Starting a business during a global pandemic, while not a mistake, isn’t necessarily recommended. It was hard, painful, and emotionally draining. Hopefully, this is not a choice most of you will need to make.
- Picking an incredibly hard problem to solve. Fixing meetings sounds easy, right? It’s such a multifaceted problem that needs to be solved holistically rather than treating the symptoms. Whenever a problem requires changes in behavior, there is an exponential increase in difficulty. We could have picked something easier, but this is what we were passionate about.
- Running a business while launching a new one. At one point, I had two full-time consulting jobs while building and fundraising for Team Huddle. While launching a startup as a side hustle is normal, I was pushing the envelope. I don’t think I’d do that again, but hey, who knows?
Tell us a little bit about your marketing process. What has been the most successful form of marketing for you?
My background is marketing, and I consider myself a marketer above all else, so this is a little bit in my wheelhouse. I’ve marketed digital ads, chocolate, wine, medical devices, financial products, and while the products all differed, the fundamentals are the same: Find the right audience(s). Find the right message(s). Get the product(s) / service(s) into their hands as easily as possible.
In terms of paid mediums, there really is no one answer here. It’s wherever your audience is looking. Keep it simple: If they are on Facebook, your message needs to be on Facebook. If they listen to podcasts, you need to be on those podcasts. And if they’re into basketball, your brand needs to find its way into the game. Go to your audience.
Messaging is even more important. Don’t focus on what you’re selling, focus instead on what your audience is looking for. Tired of paying high fees? Pitch low monthly installments. Hate how this gizmo breaks down all the time? Ours has a 10-year guarantee.
With our initial product ScheduleIQ, we’re helping people with their schedules. That means our marketing has to be straightforward; Take our message-free, human scheduling to the workplace, office and meetings themselves. While we will use paid media, our emphasis will be on organic growth through exposure and word of mouth.
What was your first business idea and what did you do with it?
Sea Kayaks. Yes, you heard that right. I was a lifeguard at a beach resort on the Mediterranean and through some good fortune got my hands on some used sea kayaks (a small oar-powered boat with a flat top that seats two-four people standing or sitting). For three summers I built a tiny water-sport empire across a handful of beach resorts. Not a multi-million-dollar idea, but it did teach me the basics of running a lean business and how to scale.
What are you learning now? Why is that important?
How people with different jobs have completely different scheduling needs. I am a CEO of a small tech company, which means I meet for a living. My ideal schedule is full of meetings, with 30-45 minutes in between to grab a bite to eat or get in a bio-break. Contrast that with a designer or developer, where 30-45 minutes between meetings is next to useless. They’d rather have three back-to-back meetings if that means their afternoon is wide open to do ‘real work.’ Different strokes for different folks.
This doesn’t just apply to our ScheduleIQ product, but in the day-to-day running of Team Huddle. We’ve had so many meetings this week, my co-founder and head of engineering asked to skip all of today’s meetings because he needs to focus on his development. I both appreciated his honesty and encouraged it. Meetings are there to support work, not get in the way of it.
What’s a productivity tip you swear by?
Don’t go to every meeting you’re invited to. If you don’t need to present, make a critical decision or participate actively in some other way in a meeting, ask to get an email recap or the notes. Your 60 minutes could be better spent elsewhere.
People feel obligated to attend meetings they’re invited to, but in most cases, hosts tend to over-invite to make sure “no one is left out.” This impacts work-related stress, as well as being financially costly to the company.
Ask to be marked as optional or removed from a meeting: “Thanks for inviting me, but I don’t believe I need to attend.” There’s nothing wrong with that. Encourage the people that work for you to do the same thing. It’ll make you and the whole company more productive.
If you only had $1000 dollars to start a new business, knowing everything you know now, how would you spend it?
Not much to launch anything really, so there are fundamentally two paths:
A – Slowly grow the $1k into $100k
OR
B – Use the money to go fundraise the $100k from an angel investor
Time is the most expensive asset, so it’s plan B for me. Spend $200 for an invite to a local event where you have exposure to investors, $300 on presentation, visuals, and business plan/financials as needed, $200 to build a prototype/mockup (no-code/website builder), and $300 for company set up on a platform like Gust Launch. Practice your pitch until you’re blue in the face with a friend and go out there and lay it all on the line and raise some real money!
What is your favorite quote?
“If you’re going to eat $#*!, don’t nibble.”
– The Hard Thing About Hard Things by Ben Horowitz
Nothing could be more true, and rarely is this advice headed. As an entrepreneur, you’re gonna have to give bad news, or make tough decisions. Company leaders, who need to be quite optimistic people, try to sugarcoat or delay difficult announcements or decisions. Just rip it off like a bandage, take the L, learn and move on.
What is your definition of success?
Having an impact.
This could mean different things for different people. For us at Team Huddle, it’s changing the way millions of people meet. For people in other jobs, it may mean being integral to the success of the business in some way. At home, it’s positively impacting the lives of your family and loved ones.
I guess that also means my definition of failure is being insignificant and not having an impact. Paychecks are important, that’s undeniable. With that being said, failure at work is the feeling that nothing would change if you didn’t show up for work tomorrow.
How can readers get in touch with you?
As I’ve been told time and time again, I’m annoyingly sociable. You can connect with me on LinkedIn or on Twitter, where my handle is @RobSmithHuddle. You can also e-mail me at founders@teamHuddle.io and learn more about ScheduleIQ at www.scheduleiq.io.
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