Big Snow Tiny Conf East – Sugarbush, VT – 2018

Every year since 2012, I co-hosted an annual “tiny” conference that we call “Big Snow Tiny Conf”. 11 other business owners and myself travel to a beautiful ski/snowboarding resort and stay together in a house. In between ski/snowboard runs, we’re talking business strategy, giving and getting advice.

It’s an opportunity for you and your business to go on vacation, get relaxed, get inspired, and get energized, all in one week!

I love the “Tiny Conference” so much, that I’m attending 4 of them this year, ranging from beach resorts, to island getaways, to snowboarding retreats. I find them so incredibly valuable, both professionally and personally.

Hence, why I created this page! I want more people to host or attend more “Tiny Confs”. If you’ve been looking to attend one, you’ll find a list of “Tiny Confs” that I know of below. Better yet, if you want to create one, you’ll find my guide to doing so!

Table of Contents

Big Snow Tiny Conf East – Sugarbush, VT – 2018

CaboPress – Cabo San Lucas, Mexico – 2018

Big Snow Tiny Conf East – Sugarbush, VT – 2017

NanoPress – Martha’s Vinyard, MA – 2018

Big Snow Tiny Conf West – Beaver Creek, CO – 2018

Big Snow Tiny Conf West – Beaver Creek, CO – 2017

Why you (yes you!) should start a Tiny Conf

Most of us work on the web. Many of us have friends and colleagues from all over the world (remote FTW!).

But there’s a certain magic that happens when you meet up in real life, in a real place, and enjoy real experiences together (experiences that happen outside of Slack chats and Zoom calls). More on what this magic is all about in a second.

First, I want to sell you on the idea of you starting your own Tiny Conf. Yes, you! Here’s what’s in it for you:

You can invite whoever you want. Pick your favorite people or invite those you want to get to know better.

You can host it wherever you want. Pick your favorite destination or do it in your home town.

You can structure it however you want. I’ll give you my experiences and preferences below, but it’s your conf! Your rules!

By their nature, Tiny Confs are, well, tiny, which means spots are limited. If you can’t attend an existing one, that’s more of a reason to start your own!

Starting and running a (not-tiny) “Conference” is big, scary, and requires a ton of time, money, and logistics. Running a Tiny Conf is none of those things. It’s easy!

Seriously. It’s not difficult to do. It’s super valuable, both for the host and the attendees.

Bottom line: I want there to be more Tiny Confs, in more places, for more people to connect. So please, start one.

And once you do, put up a landing page for it, then send me the link and I’ll include it in the list of Tiny Confs at the bottom of this page 🙂

Tiny Conferences vs. Big Conferences

Having attended over 10 Tiny Confs as of this writing, I have decided to “double down” on them as my preferred conference type to invest my time, money, and travel points on (points could mean credit card points or good will points from your spouse 😉 )

I find that I get so much more value and enjoyment from conferences with less than 30 people than I do from most of the 200+ attendee conferences I’ve been to. Don’t get me wrong, there are some excellent, well-run, “real” business conferences with plenty value.

But if I compare and evaluate them based on this criteria: “Did I get what I wanted out of this trip?” … “Will my business benefit because I went?” … “Did I have fun and enjoy my time there?” … “Would I go again?”, then I choose Tiny Confs every time.

Here’s why:

More fun, relaxation, and enjoyment

Tiny Confs are not all fun and games, all the time. More on this in a moment. But, fun/activity time, down-time, and casual “hang out” time is a key ingredient of Tiny Confs. It’s a chance to get away from the day-to-day hustle, and yes, also a break from the routines of home life. There’s real value in that, especially for entrepreneurs who have a tendency to overwork ourselves.

Tiny Confs are not all fun and games, all the time. More on this in a moment. But, fun/activity time, down-time, and casual “hang out” time is a key ingredient of Tiny Confs. It’s a chance to get away from the day-to-day hustle, and yes, also a break from the routines of home life. There’s real value in that, especially for entrepreneurs who have a tendency to overwork ourselves. Deep connections with awesome people

I often come away from large conferences feeling like I didn’t get a chance to talk to all of the people I wanted to talk to, or for long enough. At Tiny Confs, we have plenty of time for deep dive conversations, follow-up conversations, groups and 1-on-1s—all with an awesome group of fellow founders I respect. These talks and connections simply don’t happen at larger conferences, and they don’t happen in Slack or on Zoom for that matter.

I often come away from large conferences feeling like I didn’t get a chance to talk to all of the people I wanted to talk to, or for long enough. At Tiny Confs, we have plenty of time for deep dive conversations, follow-up conversations, groups and 1-on-1s—all with an awesome group of fellow founders I respect. These talks and connections simply don’t happen at larger conferences, and they don’t happen in Slack or on Zoom for that matter. Space to re-think everything

Personally, I use these trips as a chance to step back and re-assess everything I’m working on in my business. Even if my plans were set, it’s a chance to ask “what if I did this differently?” and game those out with help from trusted advisors who’ve gone through or are going through similar paths. The time away, mixed with fun activities to fill the day, really gives me the space for my mind to absorb a new way of looking at my business. I always come home with a significant change of plans and clarity for my business (for the better).

Personally, I use these trips as a chance to step back and re-assess everything I’m working on in my business. Even if my plans were set, it’s a chance to ask “what if I did this differently?” and game those out with help from trusted advisors who’ve gone through or are going through similar paths. The time away, mixed with fun activities to fill the day, really gives me the space for my mind to absorb a new way of looking at my business. I always come home with a significant change of plans and clarity for my business (for the better). A year-to-year mastermind group

One of my favorite developments has been that my Tiny Conf trips have a bunch of returning attendees. They’ve become sort of an annual 3-day mastermind session, where we can get an update on how things have progressed since our last trip, and plans for the upcoming year. We stay in touch in Slack for mid-year updates and questions too. Tiny Confs have basically become my primary mastermind groups these days.

One of my favorite developments has been that my Tiny Conf trips have a bunch of returning attendees. They’ve become sort of an annual 3-day mastermind session, where we can get an update on how things have progressed since our last trip, and plans for the upcoming year. We stay in touch in Slack for mid-year updates and questions too. Tiny Confs have basically become my primary mastermind groups these days. It’s a great deal!

This is no joke. When you’re in a group of 8+ people, there’s a ton of value to be had. You can book the nicest AirBnB in the area and the split cost is very maneageable. Ski resorts and beach resorts tend to offer bulk pricing discounts and early-bird booking discounts too. I end up spending a lot less on Tiny Confs than I do on traveling to larger conferences or family vacations (don’t worry honey, we’re not ditching the family vacations!).

8 Keys to Running a Great Tiny Conf

Here are some tips based on my experiences attending and hosting Tiny Confs through the years. Keep in mind, this is what worked for us. If you’re running your own, make it how you want!

1. Keep it “Tiny”

My favorite trips have had around 10-12 attendees. I found this to be small enough to spend plenty of time to deep-dive with everyone on the trip. This is large enough to enjoy the full-group sessions, but small enough to break into small groups of several 2-4 person conversations at times.

Also, if you plan to do attendee talks, it’s difficult to fit everyone in when there’s more than 12 talks to get through.

If you plan on housing everyone in a single AirBnB, ~12 will probably be your limit on number of beds (more on sleeping arrangements below).

I have attended ~30-person conferences, which I’d still consider to be in the “Tiny” category, and these can work well too. But you’ll need to make different sleeping arrangements and probably spend more time planning and coordinating this large of a group.

2. Make it application & invite-only

For the first few years of running our Tiny Conf, we made registrations open to anyone. For the most part, this worked out well, especially in the early days when we simply didn’t know enough people to fill all the spots.

But as the years went on and our networks grew, we found that it adds more value for everyone when we hand-curate the attendee list.

I suggest you create an application form with a few questions about their business type, size, website, years in business, and anything else you think is relevant. Then take some time to check each person out before inviting them.

While it’s great to have returning attendees, it’s also good to reserve some spots for new faces as well. That means you’ll probably need to not-invite-back some people, which can be awkward, but I think necessary. My hope is that this page can serve as a go-to referral place to send people if they can’t attend your conference.

3. Pick a fun location with an activity

As the organizer, you should choose a destination that you know and love, along with an activity you enjoy.

I’ve been co-organizing Snowboarding trips to some of my favorite Vermont destinations. Ben Orenstein started NanoConf on Martha’s Vinyard since he’s been going there all his life and knows all the cool spots. Chris Lema runs one at his favorite all-inclusive resort in Cabo San Lucas, Mexico. Pick your favorite stomping grounds and invite your favorite people!

Having a main activity as the “focal point” of the Tiny Conf helps. We spend two half-days skiing and snowboarding. In Mexico, it was swimming, eating and drinking. At Matha’s Vinyard it was biking and exploring the island. I tend to prefer some physical activity to balance out the sitting around chatting business all day. But the chats don’t need to stop… Some of my best mastermind sessions happened on the chair-lifts on the mountain!

4. “Sessions”, not “Talks”

Traditional conferences have speaks who give talks from up on stage. At Tiny Confs, I think of them more like “Sessions”, with one person leading an open discussion for everyone to participate in.

With a group of 12 or less, all attendees should be encouraged to lead sessions. We tell people they can use their ~30-minute session to talk about anything they want. Some people share an interesting tactic they’ve had success with. Some ask for feedback on their new product idea. Some ask for advice on a key strategic decision they’re wrestling with. Some people prepare slides, some just have notes, some have nothing and just talk. All of these can work!

Note: Your session will definitely not be the only time you get to talk about “your stuff”. You’ll quickly find that when you get a group of entrepreneurs in a house together, we dive right in with the shop talk and it doesn’t stop until we leave.

One of the coolest things is that there’s plenty of time for follow-up conversation after the main session. For example, someone might talk about something on night 1, then dig in more on that while on the chairlift or in the pool the next day. There’s time for both large-group discussion and small-group or 1-on-1 feedback. You won’t get these opportunities at larger conferences or workshops.

5. Plan everything in advance

Since a tiny conf can feel pretty small and laid back (and it is), it can be tempting to keep things loose and play things by ear.

Don’t do that.

Better to have a ready-made plan in place before the trip starts then to have to figure things out on the fly. As the organizer, this is your responsibility.

The reason this is important is that it can be super distracting to have to pause high-quality conversations and distract everyone with “where are we going to eat tonight?”, etc.

Pre-plan how you’ll do each meal:

Cooking in? Which groceries will you need to buy?

Going out? Which restaurant? Are they open? Should you book a reservation?

Ordering in? From where? Do they deliver to where you’re staying?

Hire a chef? How much would that cost?

Plan the schedule. Here’s my suggested (rough) itinerary

Arrival day: Easy dinner. Take-in pizza or similar. Round of introductions. Casual chats and hangouts.

Full conference days: Sessions in the morning or evening, leave a big space for open hangouts or doing the activity (snowboading, biking, beach, etc.)

Final evening: Group dinner out at a nice restaurant

Fill in the gaps as needed…

Plan the list of sessions and when each person will go. This gives folks a heads up on when they should be ready and when they can expect to have their session. Also, as the organizer, try and moderate the time. It’s very easy to drift into lengthy group discussions, which eat into others’ session time. Remember, there will be plenty of time to follow-up later, during casual hangout time.

6. Manage the money

This probably sounds obvious, but you need to have a plan to manage the cashflow for a Tiny Conf.

During the planning stage, try and put together a ballpark budget for things like the AirBnB cost, groceries, activity costs (ski lift tickets, beach passes, etc.), and anything else that will be “included” in the price of each person’s admission.

Don’t feel like you have to take a big risk and potentially lose money as the organizer. I’ve seen two strategies work equally well:

Strategy 1: Set price, budget accordingly

Based on your budgeting, come up with a flat fee to charge people up-front. Then it’s up to you as the organizer(s) to pay for all the things. Ideally, you’ll pad the pricing a bit so that you’ll have extra in case someone cancels and needs a refund, or other unexpected things come up. After several years of running ours, we’ve had surplus cash, which we’ve been able to use to keep prices down, book nicer houses, and book in advance.

Strategy 2: Split the cost as you go

If this is your first time organizing a trip, it can be difficult to predict your costs. Do what my friend Ben did at the Tiny Conf he organized at Martha’s Vinyard: Start by guauging interest with a group of friends. Then when you have enough “Yes, I’ll go”, book the AirBnB. Then ask everyone to pay their share of that cost. Then during the trip, the organizer paid for all meals on his card. Then after the trip, he added up those food costs and asked everyone to reimburse for the total.

Either way, there shouldn’t be a scenario where the organizer is losing their shirt on the trip. Nor should any attendee’s costs skyrocket unexpectedly.

7. Keep in touch before, during and after the trip

I highly recommend starting a Slack group for your Tiny Conf.

Before the trip, it’s always nice to chat and get to people a bit before you meet in person. Did I mention entrepreneurs are a chatty bunch?

During the trip, the Slack has proven essential for us. We’ve used it to communicate travel arrangements, flight delays, ride shares. We’ve used it to communicate while we’re spread throughout a ski resort, And we’ve used it to share pics with everyone.

After the trip, we keep the Slack open and active throughout the year. This is where the ongoing mastermind aspect comes into play. We post updates, questions, and continue the conversations all year long until we meet again at another Tiny Conf.

8. You do you!

I can’t stress this enough. I’ve been to several Tiny Confs organized by several different people and all had their own ways of doing things. And all were great!

Take it upon yourself to design your Tiny Conf just like you’d design a product to scratch your own itch. Make it great for you and great for your type of people.

Frequently Asked Questions about Tiny Confs

In case you’re wondering…

When is the best time to schedule a Tiny Conf?

This really depends on the destination. The main rules of thumb would be: Try and avoid holidays (most people won’t be able to make it). And be aware of smaller holidays, which tend to have higher rates at resorts and hotels. Avoid those too.

It helps to go on weekdays and not weekends. First, rates tend to be less expensive. But also, you’ll attract higher quality business owners who have more flexible schedules than those who have full-time jobs.

How do I attract people to my Tiny Conf?

If you don’t have an audience or network, I’d suggest starting in two places:

Attend bigger conferences where your type of people attend. Meet folks there and float the idea of your Tiny Conf by them, then follow up with personal invites after you met.

Be active in online communities, forums, Slacks, etc. with likeminded business owners. There are plenty of those to get involved in. Float the idea around those places to build an interest list.

Lastly, if you have a landing page, Tweet it to me and I’ll post it at the bottom of this page!

What are the sleeping arrangements?

First, you’ll need to confirm that the house rental or hotel that you’re booking has enough separate beds for the number of attendees you have. Many AirBnB’s advertise themselves as “sleeps 12” when in fact that means 6 beds that can each sleep a couple. You’ll probably need to double-confirm with the AirBnB host about number of separate beds.

In most cases, some or all people will share a room with someone else. This has worked fine in my experience. Just make sure that you’re up-front about this so that people don’t have the wrong expectation.

I think it’s a good idea to pre-assign beds to all attendees. That way you’re not dealing with a “race to the best bed!” situation. That’s just awkward and unfair to people who have late flights in.

Should business partners attend together?

I’ve been to some where business partners attend together, and this can work fine, if there is a large enough group. However, if the total group is very small, then one “company” can dominate the conversation and you won’t get a variety of perspectives in the mix.

Also, if people are opening up and asking for advice, oftentimes those questions involve partnership issues which would be avoided if all partners are in the room. Just something to consider.

What should be my first step to starting a Tiny Conf?

I’d start by talking to a few people and share your idea. Then if you think it has legs, then buy a domain and put up a single-page site for it! Slap an email form on there to collect addresses of people who are interested in hearing more about it. Then email those people and start throwing out dates and ideas.

I won’t get into how to build a website, how to take payments, how to set up a form, etc. You all probably know how to do all that, or can find resources elsewhere.

Where can I find Tiny Confs to attend?

I’m keeping a list of some that I know of below!

Other questions?

Tweet at me and I’ll update this FAQ as needed.

Tiny Conferences List!

All of those listed here meet the following criteria: 50 attendees or less (I tend to prefer those <20), business focused, has a website.

Note: I’m not aware of the status or all of the details about these. You’ll need to click through and contact the organizers with any questions.

Know of a Tiny Conf that should be listed here? Tweet me the link and I’ll take a look.

This list should be longer! Start up a Tiny Conf, then send me the link!