Jared Benoff

CEO @ Vacationeeze | Boutique travel company specializing in group travel | formerly @x and @usdol

[Jared Benoff @JBenoff]

@SMB_Attorney @smblawgroup Very cool and much deserved success

[Jared Benoff @JBenoff]

@Seanfrank I plan destination weddings for a living and the amount of joy I see when a couple is able to save money by not doing it at home AND host all their friends and family is incredible. The memories are worth it

[Jared Benoff @JBenoff]

@Seanfrank How are brands finding smaller creators at scale?

[Jared Benoff @JBenoff]

@ramit Have you ever used a travel advisor? A good one could handle a lot of this for you.

[Jared Benoff @JBenoff]

@mhp_guy Ok but what resort 👀

[Jared Benoff @JBenoff]

@KevinEspiritu @epicgardening Which revenue level saw the most things break and taught you the most?

[Jared Benoff @JBenoff]

@sam_allsopp_ Loved this. I’m 1 year in and can’t believe the sheer amount of daily decisions.

[Jared Benoff @JBenoff]

@patrickdichter Feel this to my bones.

[Jared Benoff @JBenoff]

@NiklausFuller This is incredible. What a journey and path you’ve carved.

[Jared Benoff @JBenoff]

After leaving my job a year ago, this post really resonates. Hardest, scariest, most stressful and absolute best time I’ve ever had.

[The Real Estate God @TheRealEstateG6]

After 4 years in business

Some thoughts on entrepreneurship:

- it’ll be both the easiest thing you’ve ever done and the hardest thing you’ve ever done. Easiest in that once you clear your plate of all the bullcrap (useless meetings, etc) you spend time on at a w2 job, making money actually isn’t that difficult. You should be able to easily make more than you were making at a job within your first few years. Hardest in that running a business is probably 10x harder than anything you’ve done as an employee in every other way

- you’ll finally be exposed to “reality”: when you’re an employee, you’re shielded from reality. You’re not the one people go to when shit hits the fan, you’re not the one who has to scramble to make payroll, you’re not the one who has to be guaranteed on loans, be responsible to investors, etc. All changes when you run your own business. Every problem is your problem. Reality sucks and is very stressful

- there are no longer right or wrong answers. Most people are used to a direct feedback loop from their superiors. That’s not how running a business works. Half the time you’re choosing between two horrible options and you just have to pick the one that fucks you the least. The other half of the time the feedback loop is so long that you don’t even realize you made a mistake until the business goes under. Have to become comfortable with not knowing if you’re right or wrong

- by the same token, there’s no one you can go to when you don’t know what to do. Can’t ask your MD for help, can’t even look it up online as the problems are so unique, they’re not even googlable. Have to become a crazy good problem solver. Also have to make decisions very quickly

- do not under any circumstances personally guarantee high LTV debt (especially if the loan term is short). Running a business is difficult. Over the long term, it’s very doable and I would even argue, at times, pretty easy. However, if you give yourself a short term clock and high debt service, it’s nearly impossible. Problems take time to solve. Don’t set yourself up to fail

- you’ve never done anything difficult in your life until you run a business. W2 jobs aren’t “hard”. Don’t care if it’s banking, PE, whatever. Doing what you’re told isn’t difficult. What’s hard is making the right decisions every single day that ensure the business 1. makes money and 2. is headed in the right direction. Totally different ballgame

- you’re literally always “on call”. And not “always on call” how finance people think of it where they have to come in Sunday morning hungover and format a slideshow. That's nothing. Always on call in that you spend every second of every day wondering how you’re going to pay the loan that’s coming due in a year or the property tax bill that’s hitting in a month. There’s a mental load that never leaves

- don’t expect to take a real vacation for a year or two

- you’ll realize how narrowminded you were as an employee. Everything you thought was important is incredibly unimportant in the grand scheme of running the business

- you get insane time freedom. Can do whatever you want when you want. Pretty much impossible to go back to being an employee after running a business because of this alone

- the days of the week all become the same. Sunday is the same as Tuesday is the same as Friday. Holidays are the same thing as workdays

- your work output is actually tied to making money, so it puts you under a lot of pressure to work at all times otherwise you’re leaving revenue on the table. Would recommend avoiding that after the first 6 months or so

- keep a real schedule with defined hours. It becomes very easy to let business bleed into everything. Don’t let it, will make your life awful

- overall running a business is probably 10x more enjoyable than working a w2 job, you’re going to be scratching your head wondering why anyone chooses to be an employee

- only thing you’ll regret is not starting sooner

[Jared Benoff @JBenoff]

@patrickdichter Congrats - love your transparency and journey

[Jared Benoff @JBenoff]

@mediaking Are you building sms in house or using a tool?

[Jared Benoff @JBenoff]

@RandBusiness This is awesome. Congrats on the launch!

[Jared Benoff @JBenoff]

@mhp_guy Also incredible the locations they open. Some are super small and in undesirable locations, yet attract huge crowds. Also pricing is 🍌🍌

10/10 will buy again soon.

[Jared Benoff @JBenoff]

@thesamparr Etereo. Easy flight from NYC, short drive once you land.

[Jared Benoff @JBenoff]

@StrongpointRich This was me. Closed on our first business when our baby was 4 months old; closed on our second when he was a year old 😅

[Jared Benoff @JBenoff]

@ramit 🙏

[Jared Benoff @JBenoff]

@NewRetirement @ramit 100% Many couples I speak to often have 4-6 weddings per year for a multi-year stretch. Between potential travel, gifts, and outfits, it's likely thousands of dollars per year.

[Jared Benoff @JBenoff]

Standard caveat that this is anecdotal, general, and purely based on my experience (we plan ~80 weddings per year in Mexico/Caribbean, $20k avg budget, 70 guests on average):

-Couples from HCOL cities generally save at least half by getting married abroad (ex: a recent couple was planning to spend $150K in LA, but spent $48K in Mexico). They also generally assume their friends/family have a higher propensity for travel and are a bit more likely to push the guest budget.

-When the groom is the primary driver of the conversation, the guest budget is often a lower priority compared to the overall vibe and wedding budget concerns.

-When the couple keeps the wedding small (i.e. under 40 people), I tend to see guest price as a big factor and the couple is more concerned with making sure their "core people" are there with them.

-More people invited generally means more people to please and therefore more activities, restaurants, etc at the resort. Some of our largest weddings are at the largest resorts; this isn't a coincidence.

-Generally, with South Asian weddings, guest price and vibe are the #1 and #2 factors, respectively, more than any other affinity/religious/cultural group.

Emailed you with more thoughts!