Making The Most Of Company Off-Sites: More Productivity, Less Boondoggling!

Hawaiian BeachThe sun now sets at 5pm and it only gets to a high of ~64 degrees nowadays in San Francisco. Despite the cold, winter is one of the best seasons in Northern California thanks to epic powder up in Lake Tahoe three hours away. I’ve got my season pass on hand and I can’t wait to carve it up at Squaw Valley. What’s better than shredding down a 2,800 foot vertical and then grabbing a beer with friends in a hot tub? Nothing!

Before the snow falls there’s this awkward time between November 1 – December 1 where it’s cold, but not cold enough to bring about consistent natural snow. My resort closes down for three weeks in November for maintenance and artificial snow production to build the base as an example. Can you imagine living in a cold climate without anything to do? That’s like living on top of a hill with no view.

As CEO of my business, I’ve decided to make an executive decision to host an annual company offsite in Hawaii every November to December. Going to Hawaii during the winter maximizes one’s appreciation for the islands since the weather ranges from 70 at night up to 82 during the day, everyday without fail. Hawaii is also one of my key retirement hubs I’ve got to do more research on before permanently relocating for an estimated six months a year. The other six months will be spent between San Francisco, Lake Tahoe, and traveling.

After attending a disappointing company offsite in NYC where we were locked up in conference rooms the entire weekend, I promised myself if I was ever the big boss I’d do it right for my people. A company off-site should exist to build relationships, improve profitability, and make work fun. I’d like to share some thoughts on creating a company offsite agenda for maximum business efficacy.


1) Financial overview. Analyze the month over month, quarter over quarter, and year over year sales, operating profit, and net profit figures for every product line. Is the business trending up, flat, or down? The goal is to get an idea of which products are selling best to maximize profitability and deemphasize those products which are selling poorly. Analyze the profit margins for each product and see whether they are expanding or contracting.

Getting a good grip on a company’s expenses is vital. The goal is to create an optimal cost structure so that as sales grow, operating profits grow even faster thanks to leverage. Operating leverage is the main reason why I love internet businesses and would never want to do anything else. It costs $20 a year to register your URL regardless if you have 100 visitors a day or 1 million visitors a day. We are talking 80%+ operating profit margins online. The key is to keep marginal costs to a minimum without impeding growth.

It’s also important to understand the seasonality of the business so you can adjust production accordingly. I discovered after you reach a certain traffic level online, there’s a noticeable slowdown during the summer months online given most of my traffic comes from search engines. There’s nothing I can do to prevent school from getting out during the summer and families from going on vacation. As a result, I plan to join the world in taking lots more vacation between June – September as well. I’ll probably do my other semi-annual board meeting in a new location during the summer for at least a couple of weeks to make sure I don’t slack off too much.

2) Goals overview. Compare the progress made to the initial goals. For those goals that were not completed, have a candid assessment as to why. Perhaps you were too optimistic, too pessimistic, or some exogenous variable created a change in the competitive environment. For those goals that were completed, discuss whether the goals fulfilled their purposes. Goals often change throughout the year and it’s important to make sure such goals are relevant to the business’ success.

One of my main goals is to build at least one new online income stream or one new web feature a year. 2012 was the launch of my book on severance package negotiations, and 2013 was the launch of the FS forum which needs more participation by me if I want it to grow. For 2014, I’m considering creating a subscription membership forum instead for more serious investors and a second book. Making 50-100% on Chinese stocks was huge, and it looks like serious investors are willing to pay for more such insights through a subscription newsletter or forum.

3) Goal setting for the new year. Now that you’ve analyzed the past 12 months, it’s now time to make new goals for the next year. It’s a good idea to just follow the calendar system of goal setting because the business environment, including the IRS follows the calendar system. No need to be a rebel in this regard unless you have an extremely cyclical business.

I’ve found that the higher you set your goals, the higher the outcome. Setting low hurdles only serves to make you feel better about yourself at the end of the year. What you really want to do is push yourself to the limit to see what you can do and then adjust accordingly. I like to deploy a Blue Sky, Aspirational, and Base Case scenario for my goals.

4) Team building exercises. Team building events are great to boost morale. When colleagues get along, synergies are created. You’re more likely to go that extra mile for a colleague you like versus a colleague you hate. I plan to host some scuba diving, hiking, surfing, and golfing events with my colleagues and prospective clients to build camaraderie. We’ll also have team dinners to sample local cuisine as well.

It’s hard to boost employee morale if your business offsite is in some office building where the skies outside are grey and the weather is freezing. Seasonal depression (SAD) is a real thing and you don’t want to start associating business off-sites with depression. Going to a warm place like Hawaii, Bora Bora, Fiji, Playa Del Carmen, Mallorca, South Of France, and Cabo are ideal places for team building.

5) Compensation and promotion decisions. Thanks to technological progress, competition is more fierce than ever in practically every single industry. Retaining the right group of people and not letting them go to competitors is one of the biggest challenges every manager faces. It’s important to be up to speed on the latest compensation figures and perks to stay competitive.

The company offsite is a chance to discuss with other senior management who are the indispensable employees. Employees who are up for promotion should be aware that year end off-sites are crucial for providing a final last impression. This means no getting slopping drunk at the company party. Underperforming employees also have one last chance to demonstrate their worth.

6) Acknowledging performance. It’s important to always recognize great performance. A company off-site is one of the best times to host a small award ceremony highlighting employees who truly went above and beyond normal company culture. My favorite awards are: Best Team Player, Best Culture Carrier, and Most Dedicated.

More than money, employees want to receive recognition. A simple “thank you” by the boss or a blast e-mail highlighting a subordinate’s achievements to others is a cheap and highly effective way to retain employees and keep motivation high. I strongly believe companies don’t recognize employees enough for their loyalty, dedication, and hard work.

Here are some prizes I have in mind for my colleagues: 1) Dinner and drinks for two at any restaurant on the island, 2) An all expenses paid vacation for two for one week anywhere in the world, 3) A $1,000 shopping spree, 4) A new MacBook Pro laptop, and 5) Use of my place up in Tahoe for a week in the winter or summer.


Although I’ll be away for business until mid-December, I’ll still be publishing posts here as scheduled. I bought a one way ticket because I’m not sure how long all the business activities will take. In addition to the scheduled two week long company offsite, I plan to take tours of properties and write a post on what you can get in Oahu. I’ll also be interviewing a couple accountants to understand Hawaiian taxation laws and local government culture. Island time moves slower than mainland time and I’ve got to be respectful of this fact.

I’ve already got a handful of posts I plan on publishing based on the research conducted on this off-site. The company off-site will likely cost somewhere between $5,000 – $10,000, all put on my new travel credit card of course. I’m sure we can generate much more than that in the upcoming year if we execute our plans. If anybody plans to be in Honolulu when I’m there I’d love to meet up and talk story!


The Hawaiian Airlines® World Elite MasterCard® – Hawaiian Airlines is hands down the best airlines in America. Their service is impeccable, they provide food, snacks, and drinks included in your air fare, and each seat comes with a USB charger. This Hawaiian Airlines card gives 35,000 bonus miles if you spend $1,000 within the first 90 days, gives you one complimentary bag to check-in, and a one-time 50% off discount off your companion’s air fare! Round-trip ticket prices range from $450 – $1,200, so that’s a $225 – $600 savings right there to paradise! You also get $100 off a companion tick for roundtrip coach travel between Hawaii and North America each year, 1 point for every $1 spent, and 5,000 annual bonus miles after $10,000 in annual spend. The annual fee is only $89 and I get a free round-trip ticket every couple years thanks to my travel frequency and card.

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Updated for 2015 and beyond.

Sam started Financial Samurai in 2009 during the depths of the financial crisis as a way to make sense of chaos. After 13 years working on Wall Street, Sam decided to retire in 2012 to utilize everything he learned in business school to focus on online entrepreneurship. Sam focuses on helping readers build more income in real estate, investing, entrepreneurship, and alternative investments in order to achieve financial independence sooner, rather than later.

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  1. says

    Sam, how many people work for you? If I was the only employee in my company, could I legally have an offsite like this and count it as a business expense? I’m just curious.

    • says

      Not sure. Probably best to check with your accountant if you want to have an offsite with yourself and report back your findings! I do know there should be an annual shareholders meeting. I’ve got a small team of people working with me to keep the magic alive.

  2. says

    64 American degrees is not cold at all and I would flee toward that temperature and not away with from it.

    I go to work in the dark now and come home in the dark and I am just happy that I don’t have to scrape the windows every day yet.

    As the year end is approaching I am starting to brainstorm and plan for 2014 for both my non-income making blog and my personal budget. I get pretty fired up planning when a new year approaches even though most of my goals for 2013 were a fail.

    My debt went up in 2013 instead of down and I just have to accept it and move on.

    • says

      I guess everything is relative. I can’t imagine how cold things get in Canada since it is ridiculously cold in North Dakota, Michigan, New York, and New Hampshire during the winter!

      My other promise I made if I ever became my own boss was to stop working both before sunrise and after sunset. One or the other is fine, but not both.

      Good luck with your 2014 brainstorming!

  3. says

    I think people would definitely pay for a newsletter highlighting Chinese stock picks. That’s such a difficult market to penetrate that serious investors would probably eat that up.

  4. Michelle says

    I recommend visiting an outrigger canoe club and making plans to canoe surf as a fun team building activity. Ocean canoes seat 6; surfing canoes seat 4. So many possibilities for exploring team dynamics, trust, communication, goal attainment. And then there’s the Ohana and thrill of riding waves together!

  5. maverick says

    As usual, good insight. When I traveled for work overseas we had weekends off and toured the local sights. Sometimes, colleagues traveled with me. The good times.

    Suggestion…for the early FI types, how about a post on your thoughts for year end tax planning. With a focus on how to best live off of the investments with minimal tax impact.

    Thanks in advance!

  6. says

    I’m looking forward to your report. We are planning a business trip to the Big Island early next year. I’ll see if it’s a viable retirement spot for us. Oahu is probably a better fit for us, but it sounds like the housing price is out of reach. Keep us updated.
    Can you see if there are any good multi unit properties on Oahu? How much would a 4 plex cost? Thanks!

    • says

      Very cool. The Big Island is going to still be much more expensive than Portland, Oregon unfortunately.

      May I suggest taking a business trip to Houston or the southern states? Much cheaper than Portland.

      • says

        I think close in Portland is actually comparable to the Big Island. I was just looking at a triplex and it cost $675k. It’s much cheaper in the suburb.

        • says

          Really? I guess it depends where as I usually will look for ocean views or somewhere close to the beach.

          I think it’s better if we divide and conquer. I’ll report back on Hawaii and you report back on Texas and the southern states.

    • Chris says

      Hello Joe,

      The parents are retiring out to the Puna region of HI and we’ve spent a good amount of time out there over a few trips. The big island is basically divided in two, East and West, with East being a jungle “alternative lifestyle” type paradise and the West being sun and fun. I prefer the East myself for the raw nature aspect, but the mentality is very different from the mainland. It’s almost 3rd world in mentality, but not materially, if that makes sense. Kona (the west) is about 2x as expensive as Puna for my lifestyle. Kona is more of a packaged vacation destination IMO. Fantastic coffee of course.

      Cap rates all over Hawaii are pretty bad as far as long term rentals go. Maybe 4-5% last time I checked around a year ago. I wouldn’t buy anything that doesn’t cashflow with the 50% rule.

  7. says

    The traveling that I’ve done for work has really helped me build relationships in ways that just isn’t possible over email and phone calls alone. Company off sites are really great ways to connect to your coworkers, get to know clients better, and get closer to completing goals and targets you’ve set. And what a bonus when the off site is in a fantastic place!

    • says

      For sure. Not sure if there are many company off sites being booked to Detroit over they winter. Aspen or Lake Tahoe absolutely! Got to make work fun so that it doesn’t feel like work to get more production.

  8. Jason says

    Hi Sam

    From someone with a “staffer” mentality, this exotic offsite does sound much better than the average location. I like the idea of the prizes too, that will certainly boost the morale.

    I’m still impressed that you (or anyone else for that matter) get anything significant done after they reach financial independence.

    • says


      It really is just about the challenge of doing something better and being more productive. For example, let’s say someone won a small lottery. I dare say they’d be giddy as school kids to come to work because they’ll work for the love of it and not stress as much!

      If you are a gambler, it’s like playing with houses money.



  9. says

    Enjoy the trip! I’m a big fan of Hilo, on the Big Island, and all of Kauai. If you go to Kauai, make sure to rent a 4 wheel drive vehicle and visit Polihale. It’s one of my top 3 beaches in the world, hands down. You’ll love it!

  10. says

    Sounds more like a tax deduction to me! Personally, I like Maui (Kaanapali Beach) little better. When I was CFO, my company entertained the top 30 bicycle dealers at the Acapulco Princess (Acapulco, Mexico). The executives brought their wives to help entertain these dealers. It was a great excuse for a vacation with the company paying for it. We entertained the dealers for 5 days and stayed for 2 additional days to unwind. My only (personal) expenses was a shirt I bought and I think I even put it on the expenses report. I am glad I cannot get audited over it, it was 22 years ago.

  11. JW says


    Two questions…

    1) What do you think of BYD?

    2) Do you rent out your Tahoe place? My wife and I just moved from Denver, we’ll have the Epic Local pass this year (as with every previous year).


  12. says

    “What’s better than shredding down a 2,800 foot vertical and then grabbing a beer with friends in a hot tub? Nothing!”

    Oh man, the snow is flying here in Colorado right now and I can’t wait to get back on the board. As you said, a day on the slopes followed by a beer or two in the hot tub is just about as perfect a day as one can do.

    Have you learned how to surf yet? This may be a good thing to do in Hawaii.

    I’d definitely be interested in a paid newsletter. Hit me with it baby.

    • says

      I’m a beginner surfer. I love to body board but haven’t gotten too into surfing yet bc I’m kinda lazy to lug around a board! Can’t fit in the trunk and don’t have a big vehicle in Hawaii.

      Will think more about the newsletter. Thx!

  13. says

    I’m suggesting a company offsite for my current employer. Probably going to get laughed at if I suggest Hawaii since we have 3,000 employees and small budgets. I think it would be great for us though because right now it seems like we are suffering from cubicle fever and our productivity is way down.

    Also, sign me up for the paid newsletter. Sounds like a great idea.

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