An Entrepreneur’s Guide to Getting Laid on Every Business Trip

Russell Gold
6 min readOct 7, 2014

INTRO: I like to travel. I like fine hotels and nice restaurants. I also like to spend my evenings with beautiful women. Like many entrepeneurs, I work hard and play hard. One of the best ways to slow down my manic brain is to be in the company of a sexy woman while traveling. A few years ago I stumbled upon my secret weapon for success for while traveling. Today, I share it with you.

This guide was put together based on several years of real world experience. I’ve met and had a great time with at least 25 women over my last 20 business trips. Yup, some trips I have met more than one women over a 3 or 4 day trip. I can meet girls at a bar or book store, but if we are being truly efficient, nothing beats Seeking Arrangement, or a similar site.

I’m a pretty good looking guy, 42 years old, 5’10”, 190, fit. Am I Bradley Cooper? No. Not only do I have a date virtually every night I choose to while away, my date and I both have a great time. Sex is about a 95% certainty. It is a little known fact that women like to have sex, just as much as men do, maybe more. Even on the first date, with entrepreneurs they just met in person for the first time. But, you need to lay the groundwork, do your research, and know how to handle yourself and treat women.

If you pride your entrepreneurial self on your #zeroinbox, Evernote mastery or Hubspot dominance, get your SA search skills game sharpened.

  1. PLAN AHEAD. You don’t show up for business meetings unprepared, don’t go away without doing some research. You carefully selected the hotel, the best restaurants, and made sure you reserved an aisle seat in first class on the plane. Now it is time to check out a site like Seeking Arrangement (SA). Honestly, SA could be one of the greatest inventions of our time. You can cut right through the bullshit and find what you are looking for. The site is filled with beautiful women who want to treated well, taken to a nice restaurant, have a night on the town, and then hop in your five star hotel bed. Gone are the days of hoping a hot woman will be at the bar. No more worries about approaching a woman only to find out she is married or has a boyfriend. Before you criticize the site, give it a try. You will be shocked at the quantity and quality of beautiful, intelligent women waiting to meet you.

2. LEARN TO USE THE SEARCH FEATURE PROPERLY. I like to search within a 10 mile radius of the city I will be visiting. This makes it more likely the women you message will be within a short cab or car ride of your hotel. Convenience is king, for both you AND her. Aim high, but not TOO high. If you are capable of nabbing a 5 in real life, message women who are 7’s. Even in the pay for play world, you aren’t likely to have a genuinely good time with a 9. She just won’t be into you, no matter how big your wallet is! Play in your own league.

3. REFINE YOUR SEARCH. If you are looking in New York or Las Vegas, the numbers are staggering. If you are going to Louisville, the pickings may be a bit slimmer. Regardless, refine your search for what you REALLY want. You’re an entrepreneur after all, look for what makes you most happy. For me, that would be 25 to 34, white, athletic, non-smoker, no kids, and laid back/zen. I want someone who offsets my non-stop hypo-manic entrepreneur life. Think yoga instructor/vegan/zen. I like fit girls, so that is what I go after. Now go ahead and enter the search that floats your boat.

4. CUSTOMIZE YOUR MESSAGES, AND BE DETAILED. These sites are filled with sleazy guys sending brief messages filled with sexual pleas. Crafting a better message to get your girls attention is a piece of cake. First, compliment the woman on something from her profile, NOT her looks. Prove that you took the time to read her profile. Find a common hobby or interest and mention that. Second, be very clear when you are coming to town, when you are leaving, and when you would like to get together. Make sure your message does not come across in any way like you are sending it to 20 other girls at the same time. While it IS a numbers game, you cannot let her feel that. Take your time with the back and forth replies. It is fun, and it is worth the investment.

5. LEARN TO FILTER THE REPLIES. So, unless you are really ugly, your profile sucks, or your messages are rude, you WILL get replies. This is where being an entrepreneur comes in handy. You need to weed out the girls who are just looking for money or cannot form a proper sentence. I’m not kidding. If you start your sentences with a lower case “i”, you are disqualified, no matter how hot you are. Also, if the first thing she wants to know is how much money you will give her, say good bye. Prostitutes are not on my list. There are plenty of nice girls who want to have a great night as the top priority, and some financial assistance would be a bonus. Use your hiring skills, bullshit detector, or whatever to narrow your results further.

6. STAY AT A NICE HOTEL. You probably stay at a five star or boutique hotel already. If not, start. Trust me, it is MUCH easier to get a girl back to the Mandarin Oriental than the Holiday Inn. Simple as that.

7. MAKE THE DINNER PLANS. Once you find the girl and agree on the night and time, make the reservations. By now you should have an idea if she is a vegetarian or has some other dietary restriction. Making reservations is the first sign of being in control. Women like men who are in control. I prefer casual cool places like The Purple Pig in Chicago over stuffy fine dining restaurants. When in doubt, pick a great sushi restaurant. Everyone likes sushi. TIP: Sit at the bar. It is easier to pull bar stools next to each other and get closer as the night goes on. Trust me. You also get better service from the bartender, have another person to talk to, and remove any initial first date jitters. The alcohol flows faster at the bar as well.

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8. BE COOL. DON’T BE A DICK. Don’t try too hard. Be confident, comfortable, casual. Don’t talk about sex or anything sexual. Get to know your date and have fun. This is not a race. Being a bit distant or cocky is actually a good thing. Overly nice guys and assholes finish last. Truth.

9. BE IN GOOD SHAPE. SMELL GOOD. DRESS CASUAL. These things sound obvious, but you would be surprised. Being in shape does wonders for your confidence. I work out and eat right. Why? Several reason. I’m vain. I like to look good. Here it is, ok? Feel good, look good, fuck good. SIMPLE. Hot girls want to fuck hot guys. Give yourself a fighting chance.

10. DON’T BE CHEAP. It is not about the money, but make sure she has a better time with you, than with her 25 year old bartender boyfriend. You already have the hotel, now make sure you get an Uber over the cab, hit the better restaurant, and end up at a bar or final destination that she has not been to or could not afford. You’ll feel good taking her there, and she’ll appreciate the effort. I prefer jazz clubs, hotels bars with great people watching, or a show when in Vegas. After all, you are on vacation/business, visit the best spots.

That’s it. Pretty simple. While I may not have covered everything, this should give you a great start to make that next business trip a raging success. If you’d like to enroll in the advanced course, send me a message and we can talk. If you are a woman who fits my description above, feel free to email your pics and an intro.