Why You Hate Sales and How to Love It Again


“Perhaps the next step for sales [I wish I could offer more wisdom on] is to change the perception of sales people back to a positive one.” – final words of The Sales Acceleration Formula by Mark Roberge SVP of Sales (grew sales from $0 to $100M at Hubspot) (paraphrased)



I recently had a conversation with one of my friends who runs the largest sales meetup group in the world. First of all, you need to be pretty passionate about sales to start something like that, especially since an organization like that is about knowledge over making money. He told me how he got into running the group, and mentioned that he took a completely different direction in his life after being a burnt-out account executive. He actually got two masters degrees in marketing and then realized, after years of education (to further himself from it), he wanted to get back into sales, and not only sales, but start a meetup for it. Perhaps his time away gave him appreciation for it.

I had a similar trajectory. I did sales for some amazing companies, got burnt out, did some other stuff to distance myself, only to return to it and appreciate it even more. Not only that, I’ve now read numerous books on it, I sell sales software to sales people and I’m enthusiastic about helping my customers and LinkedIn connections get better at it with my sappy essays like this…. how meta.

Yep, I’m a teacher’s pet of sales, and I’m even a vegan. So is Tony Robbins. Yikes. Pathetic. Anyways, the key takeaway here is how can you get jazzed about sales? Do you need time apart from it? After all, it’s a grind, isn’t it? After all, people reject you daily, don’t they? After all, your friends, family and the world looks at you as a greasy, chauvinistic, careless, cacophonous, cash-crazed chimpanzee, don’t they?

Well, sure – if that’s what you choose to believe.

But I don’t believe that anymore, and voila, it’s no longer a grind. I don’t get rejected (not harshly or ineffectively at least), I have friends who think I’m somewhat cool and I even appear to have an education! (did you see those mad alliteration skills above, yo?!)

So what’s the problem? Did I discover the key? Possibly. In my opinion, to love sales again, and for the long run, there’s some deep sh*t you need to take care of, and it’s going to take going against the grain. At first it might feel like taking the red pill. Trust me, do this – if you really want to crush it.

Let’s discuss some steps you can take to make you love sales again and get money. These have worked for my and many others. They’re a more predictable path than random career explorations and chance. Let’s do this.

Stop seeking money, start seeking knowledge

Taking the student mentality instead of a desperate ‘how can I hit this month’s quota’ mentality will instantly put you into a state of excitement and relaxation. You’ll look at sending cold emails as “how can I send an email that makes prospects love me”, rather than “how many emails can I send to get a buck or two”. You’ll look at goals as challenges and a code to be cracked, rather than an fear-based stressful act of valor. You might even find that you give yourself a proper education, in sales, and you can then tell others how to do it, aka be a boss! Sales, in fact is both an art and a science. Another aspect of this is what’s called the scarcity vs abundance (attraction) mentality. Which one do you think is better to subscribe to when it comes to happiness and success in sales and other areas of life?


Stop drinking Red Bull, start eating Kale

What you put in your body is directly correlated to how much you value your own quality of life, and even your long term sales productivity. Whoa Cole, not that, ‘ol hippy sh*t again! Ok, it’s not just kale. Yes, there is a perception that sales folks drink Red Bull, excessive alcohol, and stay out late. Maybe you do, and I realize it has a place and a time (I was in a frat). The problem is, as you get into the real world, what you put in your body is now matters and correlates to the vibe you put out there, how people (your boss, your customers and your friends) perceive you and decide to be influenced by you. The best sales folks I’ve seen, are pro’s at influencing people. They are role models from the inside out.

Those who go far think about hitting their quota holistically.

Get proper sleep, eat a balanced diet, exercise and make your body happy. It will lead to more energy and a better vibe for everyone around you. You’ll feel like the world is your oyster, instead of the world is against you.. Stop with the short term caffeine gain from a Red-Bull and opt for a workout, good sleep and a salad instead. Start the good feelings internally and you’ll be nice to deal with and you’ll sell more. It’s a long term game, but it’s worth it.


Stop putting yourself first, start putting others first

This is the most repeated concept in the most famous book on networking. Not only that, but in a recent sales mentor meeting I had, I was told…

“The only person who cares about you over themselves is your mother, maybe.”

“Sales people talk to customers as if their customers care more about the sales person than themselves.” (This couldn’t be more wrong!)

(He’s the top 5 Angel investor and advisor in Silicon valley, btw)

At LeadIQ, we do a quarterly webinar and event called RateMyPitch. We read hundreds of cold email pitches from sales folks around the world. The top issue with the wording is that it’s, well, a pitch. Most sales folks communicate in a way that says “ME ME ME” (self-serving, asking for something, pitching), when in fact, it should be “YOU YOU YOU” (serving the prospect, adding value).

The good part about thinking along the lines of adding value, is it forces you to think of ways to help someone, even for free, up front. One unforeseen benefit is that you’ll start to feel happier. Yes, at first you might feel like it’s a waste of time, but trust me, karma is real. It will begin to result in higher response rates, more conversations, more trust with prospects and more closed won deals.

Send a prospect a $20 gift that relates to their interests on LinkedIn. That $20 could turn into a $20K deal. Worth it? Hey, if $20 breaks the bank, how about an email that simply shares an article that might help them be better at their job without asking for a meeting.

Also, how about using this method internally? Next meeting you have with your boss, talk about how you helped someone else hit quota, or discovered a new email template format that could help the team increase their cold email outreach response rates. Chances are your boss will like you for more than just being a quota robot. Wouldn’t that be nice for a change?

Do this type of action with this mindset on 30 prospects. See what happens.

In order to be great at sales, you need to fall in love with it as a discipline and profession, just like learning a musical instrument. Treat it like a skill to master over the years, with every discovery call and demo as a rehearsal of you singing a cooler and cooler song that gets you more fans. Take care of your body and lifestyle on the inside, so you’re happy and please people on the outside because you’re glowing with good energy. Finally, focus on giving value upfront and treat people like your family. im to truly want to help them, evenif you don’t end up selling them something.

Yes, there are tactics and books you can read to better yourself in certain situations, just like there are tactics and books to pick up women and men. Working on deeper issues like those listed above are going to lead to not only better sales and dating, but a more fulfilled career and life.

This will set the groundwork to become passionate about sales unto itself, and you’ll notice you win more. While it may seem like it at first, it’s not really that hard, and it’s not going to take more time out of your day. It’s just a different mentality. I recognize this isn’t easy, or your boss might think it’s bullsh*t, and such change won’t happen overnight. I also recognize that these are pretty touchy-feely philosophies, but they’ve worked for me and many others. If enough of us subscribe to this, maybe people will consider sales to be a respected profession one day, even though it technically already is, because everyone is doing it, all the time, as much as we don’t want to admit it. If we all work on loving our sales career, other people will love it too. Let’s make sales great again.

I hope this was helpful. What helps you love sales more? 

How to Close Moonshot Deals


I recently caught up with a friend who helps startups during a very hard phase – getting initial customers. He does this for many startups. It’s not only a challenge to get the first customers; in addition – he goes after large enterprises, with little brand to back him. He was telling me about a prospect that was very publicly requesting quotes from all of his competition, and the client startup he worked with is in a very competitive market. Needless to say – to close this deal, it looked like a moonshot, and he needed some sales-ninja skills to win.

Despite all odds against him, he ended up winning the deal. He told me the winning strategy that allows him to repeat this over and over. There was a lot, but I boiled down the top 3 ways that are the easiest to implement and have the biggest leverage. Use them and win, no matter what you’re selling.

Update: I started implementing these tactics and am already seeing results, and while I do love sales already, I’m enjoying my job even more – and my prospects like me more too. Whod’a thought? Enjoy…

Show product or company evolution

One of the key benefits of a startup, compared to a large incumbent competitor is product agility. Assuming you have the engineering muscle to build something, even if it’s a small-ish feature to implement, you should tell the prospect about it, especially if the prospect asked for it at the last call. Following up and talking about new product features not only show that you care about making a great product, they show that your team is alive and innovative, and may just be around in the future, or at least the duration of their contract with you. If you don’t have an evolving product, maybe you can think of new ways the prospect can use it.

Show interest in the prospect, personally

You’ve heard of social selling, so leverage it, and don’t stop doing it when you land your first meeting. By the way, social selling means more than just finding someone on a social network and contacting them. When I have a first demo, I generally go as far as looking at their interests, liking their posts, and asking them about it on subsequent calls or emails. I also ask them about their motivations and goals at work. Taking literally 60 seconds to go look up someone’s life outside of work or asking about their goals goes farther than 95% of the other sales people out there, who go about their day robotically, with no emotional investment. Also, try and meet your prospect in person whenever possible. Show you’re human, it’s becoming less common these days.

Respond lightning fast to any request

I’ll preface this by saying you shouldn’t go dark after they buy, but it’s even more important during the prospecting, aka courting phase. This is when you make a first impression. Responding lighting fast is easy. Even if you’re swamped and write a quick reply like, “Sounds good, I’ll get back to you soon on this!”, shows that you care and want to help them. After all, sales is about helping people, not just making money, and ironically the more you try and help and think less about money or your quota, the more you’ll make, and hey, you might even feel better about yourself. What’s cooler is the prospect who’s now about to become your customer also likes you.

If you haven’t noticed, the common thread of these tactics is that they’re all based on building trust. In fact, perhaps they’re not tactics at all; rather lessons in relationship building. What my friend and I have found is it has less to do with how many features your product has or how big your brand is. Yes, you’ll lose deals that the prospect needed specific features for, but you’ll also win a ton, as long as your product has a market fit. At the end of the day, you’re going to realize that people buy from you because they trust and like you, and you’ve shown an earnest effort that you want to make their life better. The good news is that you have control over this, no matter what your outside circumstances are.

I hope these tips help you sell more. Feel free to contact me here on LinkedIn if I can help you out!

5 Things I Learned While Working for a Billionaire


I recently consulted at a startup that was founded and run by someone who sold their last company for $1.3 Billion – in addition to being a prior partner at a top VC firm. This individual was especially interesting because they invalidated all of my stereotypical billionaire assumptions.

Instead of balking at their mega success, I ended up learning valuable behaviors I could apply to future endeavors. Out of respect for this individual, I’m omitting their name and gender.


I’ve boiled down the top 5 beliefs and behaviors that I think skyrocketed this individual to their level of success. If you don’t live under a rock, you’ll find some of these principles are attributable to other wealthy/successful people. Even if you’re not aiming at Billion-dollar-goals, internalizing and living these principles can serve you well.


Keenly understands how value translates

Have you ever wondered how one product sells at a certain price, yet an identical competitive product sells for far more? This is the magic of value perception. Wealthy people understand how to create the perception of more value with a product or service. Life isn’t fair, but if you know which levers to pull, you can put the odds in your favor, with minimal changed efforts. Billionaires recognize that it’s merely a game of value.

Pro Tip: Try mentioning how much time or money your product saves your customers and be specific. Put a dollar value on it, and invest in tight, clean sexy design. You can simply ask for more money, and your customers will thereby value it more in many cases!


Isn’t in a rush

Many people in the startup space (and business in general) are in a rush. A rush to get to market, a rush to sell enough units of X, a rush to avoid their funding running out. It doesn’t need to be this way, and someone with a billionaire mentality won’t appear to be in a rush; they are calm. What’s going on underneath is a sense or belief system of abundance. The abundance mentality means that one believes whatever they need or want will eventually come, plentifully. If you believe that, you’d less likely have a feeling of always being in a rush; stressed; or in a scarcity mentality-state. Furthermore, billionaires believe in the idea of synchronicity, also known as the law of attraction.

What one believes or dreams inside becomes their outside reality. Many books and documentaries point to this, like this one. You don’t need to be in a rush if you plan properly. I will say, on the contrary, that some pressure and a sense of urgency is helpful and shouldn’t be completely avoided. There is, however; a line between a bad rush and a good rush.

Pro Tip: Try meditating and write down your thoughts, ideas and plans and then plan accordingly. Take time to visualize yourself living the results. Stop being frenetic, reactive, defensive and feeling that there’s not enough. The subconscious mind cannot process a negative, so whatever you think about, manifests. 


“If you think you can do a thing or think you can’t do a thing, you’re right.” -Henry Ford


Tight with money

Ironically you’d think a billionaire spends capriciously. You’ll quickly realize that doing so didn’t get them to that level of wealth in the first place. It’s easy to see what happens when you’re not tight with money, even if you’re rich.

When I would ask for budget for marketing or other ‘nice to have’ things, I would be questioned if there was a true ROI behind my ask, and if there was something we could ‘hack’ or do more efficiently without spending excess money.

Sure, you’ve got to spend money to make money, and at first I was surprised; we had 90% of the VC money in the bank and minimal burn!

Pro Tip: If you really look at what makes most of our country rich, it’s actually being frugal and planning well. Consider skimming This book and this book, which explain that in more depth.


Speaks their mind candidly

As you can imagine, someone that has reached this level likely isn’t afraid to speak his or her mind. You might think this type is outspoken or even arrogant. Yes, they were candid and not afraid to have difficult conversations, however it was conveyed in a stern, yet compassionate tone.


“Speak softly and carry a big stick” – T. Roosevelt

Pro Tip: Enroll in a local Toastmasters group. Toastmasters will make you more brave in front of tough audiences while teaching you how to give effective, candid feedback to people. It has paid me and thousands of others priceless dividends. 


Willing to let go

Finally, one of my favorite qualities of my Billionaire boss (and their mentality) was a lack of micromanagement. While they debated when I asked for budget they didn’t debate when I was trying out different sales strategies. 

I found that working for first-time founders, there tends to be more emotional energy in the interactions as well as micromanagement.

Someone who’s done it before is less attached to the way things are done and more attached to the results, outcome and big picture. 

Pro Tip: if you’re a manager, identify how much mentoring your report needs and act accordingly. If you’re being managed, pay attention to how you feel you’re being held accountable and if you need more or less support. 
What do you think about these billionaire behaviors? Have you worked with a billionaire before, and if so, how did their M.O. compare?

The 50th Law – Cole’s Top-Two Book Takeaways Series


I’ve been reading a ton of good books lately, and to document this while also giving your brain some valuable tl;dr’s, I present my Top Two Book Takeaways series in which I will attempt to boil down the top two takeaways from the books I read.

I just read The 50th Law by Robert Greene (one of my favorite authors), who documents the meteoric rise of the famous rapper and business man 50 Cent, also known as Curtis Jackson. He’s a household name, and you’ve probably danced to his music or drank his Vitamin water while you were drunk or hungover. The fame and riches didn’t come without a price, which he paid in a dramatic way. With that, I present my top two takeaways of the book. Enjoy.


Bad Things Will Happen. Face, Embrace, Love them

Some people catch a common cold. Some people get laid off their job. Some people get cancer. Some people get shot by a gun 9 times, once in the head. Whatever it is, living through it is step one, but step two is turning it into extreme positive energy, which few do. First: accept, then embrace your condition; let yourself hit rock-bottom. From that place, you can only go up. Use it to propel yourself. Crawl out of the hole and start living like you’ve never lived before.

50 Cent was shot 9 times by an assassin days before the release his first album. Then, out of fear, the record label he was with dropped him because of the incident. With no record deal and lots of bullet wounds to recover from, you’d expect him to be broken, despite surviving. Quite the opposite. He led himself to believe he was now truly poised for his meteoric rise. He accepted that this was an opportunity; a sign that he could overcome anything, and yet at the same time had nothing to lose. He stayed out of the limelight for safety and quietly began to learn the music business inside out, working for the record label, learning on their dime. He hired a ‘gang’ of folks to promote his new street-distributed label on the streets. He worked tirelessly; he had nothing to lose except for the passing days of his life. All that mattered now was power, and making the most of it. He knew that signing with another big label would sap his power and wouldn’t give him the true creative space that spoke to his dark, gangster story. When he learned all the tricks of the trade and his music shattered the norm, he was then picked up by Eminem, and he rose to power.

If it weren’t for facing, embracing and loving the reality of his huge setback, he would have withered. The next time something bad happens to you, make the most of it. See it as an opportunity so you can use it as a slingshot to propel you forward. 50 argues that worse it is, the better it can propel you.


The Road is Boring. Teach Yourself to Love It

50 Cent wasn’t successful overnight. He had many setbacks, one of which you learned of above. He started out in life as a hustler on the streets, selling drugs because that’s all he knew. He then turned to music to get himself into a safer, more rewarding career, and then became a business man, aligning with brands such as Vitamin water. All of this took time and patience, not luck. A true hustler lets herself slow down and listen to the reality of becoming great. 50 became a good listener and realized that when he was paying his dues, whether it was apprenticing for a hustler on the streets or working late hours reviewing record deals at the very record label who dropped him, he was learning the business. While these hours didn’t pay him very well in money, they paid him dividends in skills, which he could then use to build his own empire.

When you’re choosing your next job or project, don’t look for short term gains or get-rich quick schemes. You’ll only shoot yourself in the foot. The bills will get paid, however if you want true freedom, you must choose on the basis of skills and people who can get you ahead in a leveraged way, so you can build your own empire. Build a strong foundation, so that when an earthquake comes, the scaffolding you’ve built will hold strong, while others’ fall. It won’t come quickly, and that’s why most fail; we live in a world of distractions and quick-fixes. We’re eluded. The ultimate successful man or woman understands this and teaches their mind patience and the exponential benefits that come with delayed gratification.


Did you like these top two takeaways? Have you used them already or do you plan to? Let me know what you think in the comments.

My Top 4 Digital Life Saving, Life Hacks


There are a few things that people see me doing on a daily basis with my phone and computer. When spotted, their eyes light up; they want to know how they can do these too so they can reap the benefits. No, it’s not watching porn. Here are my top 4 simple yet powerful methods to save time, eyes, and space. You’re welcome.


Reverse your phone’s screen colors, save your eyes at night, with invert color shortcut

They say we’re spending as much time looking at a screen all day as much as we sleep. Yikes. With that in mind, you probably should take care of your eyes, to avoid joining the ranks of Zombie land. Yes, the brightness of our screens is slowly blinding us and keeping us awake. Yes, apple has taken this measure with the night shift mode for the new iOS 9.3, which is kind of like f.lux for your computer, although this is NOWHERE near as effective as the reverse colors shortcut. Check out the better option:

When texting at night, wouldn't you rather have what's on the right?

When texting at night, wouldn’t you rather have what’s on the right?

Here’s how to do it.

Go to Settings app > General > Accessibility > Accessibility Shortcut (scroll all the way down to see it) > Invert Colors (checkmark it)

To turn it on or off, just click your home button three times.

By the way, you can also do this for your mac.

Hit ⌘Command+Alt/Option+F5 > click Keyboard Shortcuts > Click on Shortcuts tab > Click on Accessibility > Checkmark the “Invert Colors” option.

To turn it on or off, just hit Control+Alt/Option⌘Command+8 on your keyboard.

Yes, this will make your eyes happier at night, and yes, it will make you look cooler at parties. Two caveats though; things that are already black, such dark-colored apps will be bright, and photos, especially of people will become indecipherable and even creepy looking. Maybe you’re into that, you sick creature, you.


Throw your wallet away, save space with an iPhone sticky wallet, get your pockets back

Let’s face it, physical cards are becoming a thing of the past. If you really think about it, you probably only need three cards with you at any time: a debit/credit card [form of payment], your driver license/ID[form of ID], and maybe health insurance. The rest, such as your Walgreen’s Club Card and Petco pet super saver card can be stored digitally on your phone.


Maybe this is why your dating life has been sucking lately? Time for something that won’t misshape your ass.

Enter the iPhone sticky wallet. Look at how sleek that is, and how much space it’s going to save you.


That phone has a misshaped ass, but I kinda like it.

Plus, no more lost wallets.

Buy one online for a dollar, or do like I do: nab a few from a booth for $0 when you’re at just about any business conference. Companies hand them out in droves.


Kick your Facebook addiction once and for all, save oodles of time, eliminate FOMO with these apps and plugins

If you’re reading this post, you likely saw it on Facebook, so you’re probably addicted. It’s okay, I was too. First step is admission, right? 

On your phone:

Delete the Facebook app > then, only access Facebook from safari browser

This will make your browsing experience less desirable because it’s not ‘native’ and smooth like it is on the app. Plus, you won’t receive notifications. These factors will make you check it only when needed or are really bored – which is how you should treat Facebook, if you’re addicted.


Not to worry! Yes, FOMO is a terrible feeling, but you can have your FOMO-free cake and eat it too if you sync Facebook events to your calendar.

Here’s how to on Google calendar, or download Sunrise calendar and connect your fb account. I like Sunrise better because it works on all devices, even your computer. It also syncs with other event apps like Meetup and Eventbrite, plus you can rsvp to Fb events directly from the app.

On your computer:

Oh yes, there are fancier addiction cures for your computer.

If you’re using Chrome, download this Chrome extension.

It will limit your time on Facebook by how many notifications you have. Once you’ve had ample time to catch up on notifications, it will dim the screen and give you shit.

Gosh, fine!

Gosh, fine!

By the way: if you run a business that relies on Facebook, sure, maybe you need to be on there more often. If that’s the case, schedule the time you spend on there, and you may want to enable the newsfeed killer, which will simply disappear your newsfeed – the most addicting part of fb.


Save time, fingers, turn Siri into your butler, be a boss, hurt no one’s feelings

You’re probably not using Siri to its potential. Sure, your phone is happy to let you tap, type and swipe all day, but in many cases, this can simply be delegated to Siri, saving you 10 seconds here, 5 seconds there, and maybe even a minute in some cases! That all adds up in our digital, fast paced age. Save time, eat more vegan pizza. 

Go ahead, feel like Bruce Wayne.

Go ahead, feel like Bruce Wayne.

Here are a few common ones you can remember to practice your butler bossing skills and save time as if you’re a busy person with greasy pizza hands. 

Set an alarm for X:XX

Remind me to xxxxx on x/xx at x:xx

Give [Navigate] me directions to…address, city, state

Open [app name] app

Send a text to First Last saying xxxxx


So there you have it, my top 4 digital life-saving, life-hacks. You can implement them in minutes, and they’ll save you hours of time…that is, until the government puts a chip in your head, making phones/computers (and these life hacks) obsolete. Til then though…

The 2 Easy Ways Guys Can Improve the Quality of their Dating Life


First of all, what straight guy doesn’t want to make a woman he’s interested in happier (therefore more interested in him)? That’s what I thought. Read on. A big portion of this post was inspired by reading Aziz Ansari’s book, Modern Romance. You may know him as a popular comedian, yet he also commissioned an extensive and surprisingly scientific study on dating. That, in addition to input from friends and personal observations have led me to the two most simple yet powerful things that men constantly mess up but can fix easily. Don’t worry guys, it’s not all your fault, but you still need to man-up and take responsibility; because that’s kinda part of being a man, right? Sure, there’s plenty of things women could fix too, but that’s on them, not us.

By following these two steps you’ll have a positive impact on women you date – faster than you can microwave a Mac N cheese dinner, aka the time it takes to read this post.


Create an emotional connection, or two

Ever listen to women complain about men just wanting to hook up, or how they want to wait until the 3rd or so date? It’s because they’re wired differently, not necessarily because they don’t want to get physical with you. Deep down, they’re looking for an emotional connection, or a way to relate to you, and in many cases, it simply takes a date or a few to form that. That way of relating to you could be the fact you both like Fish Tacos with extra Sriracha on them, or it could be the fact that you both came from broken families and are stronger for it, or it could be the fact you have a litany of such things in common, maybe simply the right astrology match. Whatever it is, make the connection and the courtship experience will be much more pleasurable for you both.

Maybe you don’t have anything in common, but you’re really attracted to her for some reason, well, then listen! Listening shows interest. If you’re interested, then you’ll connect, and maybe even want to make yourself have something in common by doing something she already likes doing with her.

Yes, you’re a guy – you love and want sex, but after learning to be a bit more present and mindful, you’ll see that no emotional connection makes sex suck. If you haven’t already, you’ll see that it sucks for you too! No one wants that, except sociopaths and rapists. You not one of those. Furthermore, who doesn’t want passion? Passionate love-making or even passionate hooking up that’s truly consensual in our adult years almost always comes from a strong emotional connection.

If you don’t already know what it means to make an emotional connection with someone, then start asking, and begin listening and reading others. You’ll eventually get it, internalize it, and the special someone who comes in your life will value their interaction with you much more. Learn to see things from a woman’s perspective. A quality woman will also try to see things from yours. Meet each other half way if need be.


Be more precise with plans and intentions

Yes, women still like and expect men to make the first move and plan things, even feminists! Aziz reports most messages women receive online or on texts are, “Hey”, and “Wanna hang out sometime?” Now, if you were a woman, receiving that 10 times a day, not only would desensitize you from these bozos, it would straight up annoy you. This is happening at mass scale, today. Yikes!

What if a man said, “Hey Dana, I really like your profile picture with you eating that delicious salmon dish. Want to meet up this Saturday for a bit and walk around the farmers market on the embarcadero to get to know each other around noon? There’s some incredible seafood there, you might like to see it. Let me know. Looking forward to chatting more.”

When you’re precise and thoughtful, not only do you stand out from the bozos who just say “Hey wanna hang?”, you also exhibit other universally attractive qualities: you’re seen as a leader, assertive, creative and thoughtful. Maybe you’re thinking it’s too aggressive to open with this or after just a few messages. You’re wrong. Women dislike the opposite; the chatty-cathys who never ask to meet up and just say “Hey”. That’s now the norm, be the exception. Take my advice and be precise. Also take comfort in the fact most dating coaches advise their clients to limit online messages to 6 before proposing a date.

Now, let’s say you actually just want to hook up. That’s okay! Same rule applies. It might take more finesse than, “Hey wanna bang?”, but at the end of the day, straightforward men with clear intentions are less likely to creep a woman out. Creeped out women never sleep with men, no matter how horny they are. If the woman wants to hook up too, she’ll be glad you’re upfront and likely say yes if she’s interested. Tinder wouldn’t be so popular if no one wanted to hook up.

Ever see a relatively unattractive guy walking down the street with a woman he doesn’t seem to belong with? He probably followed the simple advice above. It’s proof that inner qualities can beat chiseled cheeks.

By the way, being clear with plans and intentions translates to being successful in all other areas of life. Give that a ponder during your next meditation retreat. Did I just save you a trip to India? Yes, I accept donations ;).


“Match.com will bring more love to the planet than anything since Jesus Christ.” Gary Kremen, founder of Match.com in 1995


Maybe he was right. 1/3 of Americans used online dating in the last several years, and it has given us more options than our parents ever had. Unfortunately, there is a dark side that’s eating away at one thing many deem more sacred than anything else – love fulfillment and finding ‘the one’. In the old days, our parents just met at the school dance or via newspaper ads and got married after a few dates. Ironically they, and people subjected to arranged marriages report high levels of happiness and satisfaction in their mates. But why? This makes no sense. It’s because of the principle of scarcity and less options.

With so many options now, understand you’ll likely devalue humans to a mere chat bubble on your phone. In addition, many people use online dating to pass the time or keep one eye open for something better out there; an upgrade. 

Hey, I’m really enjoying T100 right now. 

-No dude, T200 is way better! 

Men and women share this affliction. Maybe you’ve already caught onto this yourself. It leads to the behaviors above like the “Hey” and “Wanna hang out?”, and lack of emotional connection. What online dating is secretly perpetuating is quantity over quality. Online dating is merely an introduction platform, but people act like the date takes place online. It should take place in person.

We’re missing and forgetting about quality. We want it back, but are seduced away from it by the allure of this feast of humans in little chat bubble form, accessible at the swipe of a finger, and dumped for the next by a swipe, goodbye text or silence. We must consciously tune out the noise and the plethora of options we’re now addicted to and treat them as an illusion; a hedonist treadmill with destination: emptiness.

Everyone has good and bad qualities that you’ll like and dislike. It’s good news that we have more choices than our parents and ancestors, and can now select people with many more similar qualities and interests, but you’ll need to recognize when the time comes; you want a fulfilling, quality relationship – you’ll have to tune out your addiction to instant gratification and always looking for the next best thing. The perfect match might already be in front of you, if you just give them a bigger chance.


Cole has also written about the fallacy of online dating, as well as some deeper, tougher-to-attain qualities men can develop to attract the woman they desire.

The 4 Difficult Yet Effective Ways Men Can Attract Modern Intelligent Women


Dating sucks, they say. Don’t live in a city to find your significant other, they say. Don’t online date, they say. I thought I would perpetuate this trend with another incendiary blog post to entertain my friends, but then a close friend stopped me in my tracks: “Cole, you’ve dated a good amount, and you’ve got some smart things to say. Why don’t you give advice, rather than just join the chorus of complainers?”

I aim to follow my friend’s advice with this post. I hope it’s helpful to you.

Before I get going with my lovely list of do’s for men, I want to clear up a couple things. First, I am a heterosexual male living in SF. I don’t know if this advice may not work for LGBT folks, and it may not work for folks outside of ‘modern’ places such as cities like SF and NYC where dating culture and expectations are different. Furthermore, this article is not about pickup tactics, which have been written about extensively. Such tactics might be fun to use at a bar, but they don’t work on intelligent women or the path to something emotionally fulfilling. Finally, at the end, I’ll share one REALLY EASY wild card way to date if you live in the city as well as a fun troll-worthy chart (everyone loves easy fixes n’ charts, right?) Without further ado, let’s dive right in.



Don’t know what integrity means? A great example to start with is keeping a job or a career path (if it’s in your control). One of the keys to success in life is sticking with something, no matter how hard it gets. Women sense a man who has this core philosophy and instantly attribute the fact that you’ll actually be able to stick to your potential relationship with them through the thick and thin. I recall asking a really desirable woman in college why she dated a guy on the track team. It wasn’t for his body; it was for his commitment to the sport. She found it magnetic. I’ve noticed that now that I’ve become a morning person, women respect my wishes to stick to it; even if they have zero intention of becoming one. As DJ Khaled says, “I will never stop”. That’s pure integrity. Don’t have integrity? That’s okay, learn to build habits or find someone who can hold you accountable to something, like a mentor.



Those who seek advice are usually folks who want to grow. Mentorship can come from an expert, but it can also come from being a mere sounding board. I’ve found that when I listen and give advice on a situation, whether it’s work or personal related; even if I’m not an expert witness or a licensed therapist, it’s deeply appreciated. It adds value to their life and shows you care about helping them improve their wisdom. You should seek advice too. It will only enrich your relationship, even if you’re just dating casually. Next time she asks for advice, listen and react without your personal agenda. It’s easier than you think. You’ll be surprised how easy it is to give good advice when you’re merely a sounding board. Pro tip: better sex comes from a stronger connection.


Emotional Intelligence

Women might be experimenting with their gender roles, but straight men aren’t. They’re still trying to be the tough guy who doesn’t show or care about his emotions. This is not only a bottleneck to keeping a woman attracted, studies now show it’s physically unhealthy for you. The modern man seeks to understand his emotions and isn’t afraid to talk about them. He understands that modern women might have some masculine and feminine qualities, and he may too. Go ahead, open up a bit after some rapport is built, even if it’s just date #3. When a man reveals deep psychological traits about himself, it’s rare, and women feel closer to him, therefore more attracted. Do you know if you’re an introvert and if so, when you need space? Do you see the world emotionally or logically? If she’s repelled when she finds out about such traits, she’s simply not right for you. Some places to start are learning about your zodiac sign, your myers briggs and love language. Class is in session!



The better you are at saying FUCK YES or FUCK NO, the better off you are. <– read that linked post after this btw. Integrity and Passion go hand-in-hand. You’ll only have integrity if you’re passionate about something. Ever heard of that saying, “You only get what you put into it”? Well, the same goes for every single part of life; dating, work, etc. When you have a passion for your work, women notice. When you have a passion for a woman, she’ll notice, even if it’s not immediate. Sure, you can go for something, but it will come to you more quickly if the quality and intensity you go for it with is higher. Combine this with the 3 traits above and you’ll be attracting the ‘hard to get’ women in no time. Not passionate about work? Take up a hobby like Piano or Snowboarding. When you’re describing your passion for it, that’s magnetic. Finally, when you’re passionate, you’ll be more likely to act chivalrous; making subtle affectionate efforts; such as holding the door and carrying things.


Wild Card

It’s simple. Date someone who lives outside the city. I’ve had great luck with this. Why? If someone lives in the same city, chances are they’ve experienced the same things, gone to the same places for dates and maybe even have a few friends in common to you. On top of that, modern, ambitious city folk are very selfish with their time. If you start off with the pressure of living walking distance from eachother it might feel overbearing. These are all factors that seem to kill city romances. When you date someone who lives outside the city, even by a few miles, they will see dating you as a new adventure and the allure will be strong. Things will more likely start of on the right foot because of the vacuum between you, rather than the idea of over-saturation. I’ve seen the benefits first-hand. Give the ‘long distance’ thing a try, despite its bad reputation. You might like it.


In conclusion, I recommend working on the areas mentioned above if you really want to attract someone who enriches you, and you won’t feel like you’ve settled. Love is a two way street, and you’ll only end up attracting and keeping the quality of person that you first build in yourself. Most people don’t consciously work on themselves in order to attract others, they think it’s just a matter of a few pickup lines and how many sit-ups they do. After dating a lot, reading psychology books and quizzing countless friends of mine, the above is the best advice I can offer you, boiled down to 4 of the top factors.

If you’re still not convinced, take a look at this satirical diagram I made, which will hopefully make it more clear:

Man Vs Pickup Artist

Did you get this far? If so, and if you’re a straight woman; I hereby challenge you to write the other-sex top 4 difficult yet effective ways a woman can attract the modern man. Perhaps there also may be a versions for the LGBT community. (See my rainbow usage above? #love) Thanks for reading erryone!

How I became a Morning Person


One of my 2015 new year’s resolutions was to wake up early every morning. Initially, I read some books and even asked my network how they became a morning person. The most common answers I found were “Just do it”, “Get a dog”, or, “Have kids”. I decided not to follow that advice. Luckily, by August I was consistently waking up by 5am. It wasn’t an overnight success, but I’m really happy about the results, my quality of life and sleep has all gone up. Many people now approach me asking how they too can become a morning person. I’ve decided to reveal the secrets I learned on my journey, and don’t worry; they’re do-it, kid and dog-free! I hope your journey to habitual, fulfilled morning person can be even quicker than mine as a result of reading this.


Start With The Why

First, ask yourself why you want to be a morning person. What are your long-term goals? Are you trying to be a high-powered exec that Forbes writes about one day? Maybe you just like peace, quiet before the rush hour starts or just want to go run and see the sunrise every day? Are you getting older and want to seize every day to its fullest potential? Whatever the reason, it should be something that makes you happy and fulfilled, since being a night-owl or inconsistent sleeper is obviously afflicting you.

Here are the top reasons I became a morning person:

  • Endless studies that show why most successful people wake up early
  • More time to exercise in the morning  – I prefer AM exercise
  • Higher self-esteem; since I feel like I’m the first one up before all else
  • The calm feeling that my day isn’t scrunched

What’s your why? Figure it out and focus on it.


Do Some Calculations

Find out how many hours your body needs to get a good night’s rest. Some people only need 4 hours, some need 10, most need 8. Pick a weekend or night you don’t really have any next-day commitments, don’t drink or do anything to affect your sleep quality, then wake up without an alarm clock; naturally. The amount of time you sleep and wake up naturally is about how much you should assume you need to get a proper full night’s rest. If you’re not convinced, take an average over a few nights.

Some may argue they can run on less sleep, but most argue the opposite. It’s common sense that the quality of hours in your day is better than a quantity, at least for those of us who need to use our brains in our life. It’s important to get enough rest so you’re functioning at your best; sleep is core to this.

Once you figure out how much sleep you need, it’s time to decide what time you want to wake up. If you want to be a morning person, you’re likely targeting 4am to 7am. I wake up at 5am.

Now, count backwards with the hours of sleep you need for a good night’s rest and go to bed at that time. For example, I need 8 hours of sleep and want to wake up at 5am, therefore I go to bed at 9pm. Need a jump-start falling asleep at your desired time? Take a melatonin pill 30 minutes before your desired bedtime. It’s easy on the system and doesn’t have any drug reactions, but do consult a doctor if you’re concerned.


Forge Some Weird, Yet Inspiring Rituals

Rituals are meant to bullet-proof your day and the core to looking forward and becoming a habitual morning person. They will become habits that your body will crave if it doesn’t get to do them. Pick some, all or none of these, but get some ritual going, regardless. The most famous people in history take their rituals more seriously than their religion, if it’s isn’t their religion.

  1. Alarm Clock: I have a super loud alarm clock set for 5AM strategically placed across the room, far from arms reach. No snoozing allowed!
  2. Music: I put on this playlist, full of energetic songs that fuel the emotions I want to have about life.
  3. Supplements: I eat a half scoop of this protein and this pre-workout energizer, then some creatine. It’s my coffee alternative.
  4. Care: I floss and brush my teeth
  5. Affirmations: I write down affirmations. Make your own, but here are a few examples to look at. I read some of them inverted and stare at myself in the mirror. Super intense, but make’s ’em stick!
  6. Exercise: Mondays I run, Tuesdays; weights, Wednesdays; Yoga, then I repeat. 1 rest day/wk.
  7. Superfoods Breakfast: Monday, green foods super smoothie, Tuesday, Eggs and Oatmeal, then I repeat.

These are my rituals and I follow them religiously every day. What will yours be?


Temporarily Break Up with Your Routine

After you’ve experimented with what works for you and start to build the habit, you need to purposely take a day off and closely monitor how you feel without your routine. Do you feel guilty that you’re not doing it? Do you feel a void without it? You should miss not having your morning routine and should now appreciate why you are forging it in the first place. Just like you don’t truly appreciate your lover ‘til you let ’em go, same goes for becoming a morning person. This is essential as you go through the hard phase of forming the habit. Make sure to feel this void at some point in your journey to attainment, or it might not stick.


The Fine Print

The instructions listed above might not work for you immediately or ever. You might need to try other things that work for you. Think of this journey like creating an invention. You’ll need to strategize, fail, iterate, and build. Your routine may change over your lifetime multiple times, too. You’ll need to experiment with different things that inspire you, do some self-assessment and then re-build that as a habit. Habits take about 25 days to form, and are like a lop sided bell curve, skewed with the steep side on the beginning. Furthermore, you might need to consider some significant lifestyle changes and say no to your night-owl friends more often.


The Good News

Once you get through the challenging habit change, it’s smooth sailing. It will change your life for the better. You’ll get more done, and you’ll feel better about yourself; at least 10x more, and that’s priceless. Good luck and let me know how you do.

The Fallacy of Online Dating


From 2008 to 2014 I was a member of online dating sites like PlentyOfFish, Tinder, jSwipe, OkCupid, Match.com and any other one that was stupid enough to allow me on it. I went on over 100 dates, and I got really good at *not* being nervous on a first date, and met many people. There was value in that, but none of these people stuck around. None. I also listened to many friends who complained about their results with online sites when it came to finding something meaningful. They had no luck finding something that lasted. My estimate is that 10% of my friends have found something that lasted from online. Congrats. I am happy for you, yet that’s close to the metric from Pew Research that only 5% of americans get married from online dating sites. The point of this post is to articulate why the odds are heavily stacked against you if you’re relying on online dating to find that special someone. 

Online Shopping

Power in numbers, right? No. Welcome to the commodification of love. When computers first came out they were really expensive, like the price of a car. Then, after millions were manufactured, they dropped in price and value per unit. The same principle applies to humans with online dating, and it’s happening now because we have millions of single humans at our finger tips, and it’s de-valuing us, ‘per-unit’.


Go ahead, click, swipe…you might hate what you find.


More Risk Committing

People you meet online don’t have close friends in common with you, and your common friends don’t introduce you. The danger here is that you’re dating someone without a background check. Sure, you could go scrape their court records, however that’s not nearly as meaningful as a full-on yelp-style recommendation from your friend or friend of friend who’s hung out with this person on 100s of occasions, and knows them.


Less Risk Committing

On the flip-side, once you do find any issue with an online-someone you’re dating, you have an easy out. When you meet someone online there are usually no shared connections, so if you decide to dump them, your best friends are much less likely to know, care, or judge because you don’t share this mutual friend with them. If you don’t like how they snore, that is a lame excuse to tell your mutual friend that’s the reason you broke up. If you met them online, then, who cares? Bye!

A False 1st Impression

When you look at an online profile, you see their pictures, some interests, and a free-form statement about them/what they want. Most people brush up their photos, and are generally bad at articulating the story of their life and deepest desires in a clear, effective manner (especially in 500 words) so this is going to be the wrong impression. When you meet someone ‘organically’, aka in person for the first time, without have seeing pictures or their silly blurb of their life, you pick up on things like mannerisms, vibe, jibe, personality and other things that actually matter in a relationship, like “I could actually stand to spend more than a few minutes hanging out with him/her”. Since you form the wrong impression with an online-first impression, it’s going to more likely lead to becoming a bad match down the line, when things actually matter.

That sexy rich Stanford graduate may be a type-A-perfect-force-of-genetic-perfection on paper, but terribly annoying to you after a few hours of in-person interaction, yet you stick it out because your identity wants it… Is that happiness?


It’s Not Time-saving

Many people claim they use online dating to save time finding a mate. Have you looked at how long you spend on facebook? It’s meant to be addicting and online dating sites are designed the same way. If you get home, spend a few hours browsing profiles and responding to messages, and then respond to more messages througout the following day, you should realize that time could be spent going to an event, social activity or going out with your friends to meet their friends. The math is simple.


There’s No Chase

When I say ‘chase’, I don’t mean playing games. There’s a difference between people who play games to manipulate, which comes from a place of insecurity and lack of maturity. What I mean by chase is dealing with and cutting through mystery of knowing if someone likes you, earning it, and the “f*ck yeah” enthusiasm that comes from going for something you really want, that you want to fight for. This is needed when you meet people in the real world. When you meet someone online, all of that goes away, and it’s simply a yes or no. Some people don’t want that, they want no chase, they just want ‘a human companion’. have been successfully married (for lack of better success metrics – relationships are hard to track) As humans we need some mystery and challenge to appreciate and rise up to be our best selves.


Concluding Thoughts

If you’re in your 20s, in a city, looking to hook up and explore who’s out there, then by all means use online dating apps and websites. If you’re looking for that special someone, the odds are stacked against you. Avoid subconsciously devaluing people, and don’t look for people who ‘look good on paper’ aka online. Look for someone who you’re actually willing to fight for. Just like anything else worthy in this world, you’re going to have to work for it, b*tch.



PS: here are some ideas on how to OFFline date. 

The Emotional Checklist to Become an Entrepreneur

Becoming an Entrepreneur is not easy, we all know that. The hardest part isn’t coming up with an idea, finding amazing people to help, or the work you do to launch it. Success comes mostly from tuning your mind, and how to process your reality. I’ve watched many people at our code-free hackathons fail to continue on with their idea, even after winning an amazing prize and or getting their app software developed FOR FREE. I’m writing this because I think they would be more likely continue and significantly increase their chance of success if they had the ‘mental-sweat’ tools to go forth and execute their idea.
Here are six key steps that can significantly change your emotional state to be an idea-warrior, to propel you forward during the tough times. Follow and adhere to these before and while pursuing your idea!

Get Your Parents’ Blessing

Most people subconsciously follow their parent’s wishes. They raised you, so it’s not easy to downplay their influence. My sister got married to a guy who looked great on paper and my mom loved the guy. Unfortunately my sister divorced him when she realized the guy matched Mom’s wishes, and not her own.
When I was ready to leave my cushy job at LinkedIn; arguably one of the best companies in the world to work at, my mom wasn’t happy. She encouraged me to stay, as any worried mom would want. I went ahead and left to join the startup space. Unfortunately every time I talked to her it was like pulling teeth. She told me it was not smart to leave a great company like LinkedIn, and I should go get a MBA. I began to avoid conversations about my career with her, and it was draining to think about her opposing opinion to my goals when I was trying to push forward in the startup world. One day, I sat down with her and really explained that happiness is the most important thing to me, and it’s not a 9-5 job, even if it’s at an ‘amazing’ company that ‘looks good on a resume’. I also approached her with a solid plan as to what I was up to.
After empathizing with her perspective and eloquently explaining what my career means to me, she understood. I can now freely seek from my mom and not feel like I have to avoid it. It’s a gift to your subconscious to have encouraging parents, even if they’re not a business partner or a source of good advice.

Be Cause-driven, Not Material-driven

There’s a difference between an entrepreneur who sells burritos and gloats about his piles of cash, compared to the entrepreneur who sells burritos and gloats when his customers tell him how amazing his burritos are. This is more positive, not selfish and is the difference between an abundance mentality and a scarcity mentality. Thinking this way is going to help you get up every morning, be happy, and love your customers, since they love you. They will see it on your face. Check out Simon Sinek’s talk on the “Why” of a business. It might change your outlook, in a great way. Do you know your company’s “Why”?

Only Choose Ideas You’ll Regret NOT Doing

Your idea may not change the world. It could be as simple as selling burritos from a food truck or it could be the next social network that governments use to attain world peace. Either way, the idea needs to be bothering you enough so that if you don’t do it, you’ll regret it. See Jeff Bezo’s quick talk about his regret framework. It’s why he started Amazon. Being choosy about what you pursue will help drive your passion to do it, and keep you from focusing on an idea for weaker reasons. Often times, if you work in a job for years, you’ll become an expert without knowing it, and find an idea that could vastly improve what you (and many others) have been frustrated with all along. Focus on that frustration to propel yourself to go solve the problem.

Have an Improvement Mentality

Entrepreneurs have ideas and are successful because they’re always viewing their world in a better way than it is today, both in their personal and professional life. Stagnant-minded people who aren’t interested in trying new things, or thinking of new ways to look at things are ripe for failure. You can’t be the type who waits to get told what to do. When I was working for others, I would always be thinking about how processes could be improved. If I wanted to remain an employee the rest of my life, I could just wait to be told what to do and not think about how to improve things. Find others who have a similar mentality or read books that talk about this.

Seek Out a Support Group

Your support group should be people who encourage you, and are also entrepreneurs, or at least great sounding board. Avoid close friends, romantic partners or family, since they may be biased at group meetings. You want a place where there’s pure honesty and lack of bias. Napoleon Hill, one of the most famous business writers of the 20th century, calls this the mastermind principle. Check out meetup.com to find people, or attract a group of your existing business-y friends that can meet monthly (at minimum) to talk about business issues and solutions. This isn’t all that different than an AA meeting, except drugs shouldn’t be involved! I do this weekly and it works wonders to have a white space to talk and socialize ideas in such a focused way.
Good luck and let me know your thoughts or additions to this list in the comments below. Connect with me if I can be of help. This also appears on my linkedin blog post.