It's taken me this long to actually get to sitting down and writing down the definition of an asshole.  Assholes exist.  I, like many people, figured I'd be able to recognize one when I saw one by trusting my gut.  It's an intellectually lazy thing to do, to assume.  And I have been regrettably intellectually lazy about this.  Because, assholes sneak pass my crappy filter and when I catch them, the stench is real.  Then, I break off all contact and fully disassociate with that person.  It's a crappy experience and process.  
Now that I'm in my late 30s, I thought, let's sit down and really think about this. There's got to be a better way.  It's even applicable to the world of entrepreneurship and startups.  When I applied to accelerators, they told me that assholes were not allowed.  When I talk to the professional investors and super angel investors, they tell me that assholes are not allowed.  

So I went back and documented all the different ways to tell if someone is an asshole.  I also interviewed investors, people, and other thought leaders.  I vetted the thinking with some more people.  And, by the way, Google defines an asshole as: "an irritating or contemptible person".  If any one or more of the 8 below identifiers go off, you're most likely dealing with an asshole. 

Here are the 8 asshole identifiers:

1. Relentlessly selfish.  These people don't really know how to think about anyone other than themselves.  It's me before we, always.  
2. Win at any cost to others.  They care about winning at any cost.  If they had a choice of winning where everyone else lost, they would choose to take their winning without any regrets.  
3. Love of money.  This person also loves money.  If there's a way to get it, they want it.  They want to be friends with rich people.  They are obsessed with looking like they have money.  They want more money, for themselves.  They count other people's money.
4. You should know, I'm really cool.  This one is a tricky one because when you meet this person, you find them so fascinating all of your filters turn a blind eye. Generally, the first few impressions a person tries to give other people don't start with, "I'm a visionary.  I got to party with Richard Branson last weekend.  I was eating fried scorpions in Peru before my trip to Aspen."  
5. I don't care to listen to you.  Pretty straightforward.  This person has the mantra of "my time, my words, my everything", are more important that you.
6. Disrespectful of others.  Also pretty straightforward.  This person will treat other people disrespectfully - especially the assistant, the parking attendant, the waiter, the janitor, or the kid's school teacher.  It's another version of <me> is much more important than <all other people>.
7. Cheaters.  They are missing the ethics gene and will use any short cut they can get at to increase their chances of "winning" money, fame or any success.   
8. Manipulators of insecurity.  The person that says, "You can trust me" is usually lying.  The person that says, "I'm a professional" is usually not one.  The person that says, "I support you" is usually out to get something from you.  The person that says, "I will never hurt you" will hurt you. 

If you run into a person or you identify with one or more of the above identifiers, you're probably dealing with an asshole.  Awareness is the first part, everything after that is your opportunity to make an intentional choice.  Mine will be, walking as far away as possible and never looking back.

Arry
P.S. Many thanks to my friend Minda for her contributions of intellectual ping-pong and critical thinking spent talking about this topic.  It's with her collaborative brain that I was able to get this article done.

This evening, I was on a panel titled, "The Growing Gender and Race Gap in Seattle's Startup Scene".  I got to share the panel with some amazing people.  Then as I was on my ride home, it dawned on me that maybe, just maybe, the challenge with the whole not enough "minorities" getting funding (across the board from arts, nonprofits to startups), is that this game we are in is actually like dating.

Seriously, humor me for a minute.  

Fundraising is like dating.  There's usually two players in dating - one doing the pursuing, one doing the being pursued.  Sometimes you go back and forth in playing a role.  

MAYBE women (for example) are struggling to get funded because we (most of us) are not used to doing the wooing, like men are.  Maybe women have less practice and socialization with this.  Maybe?  Some of us are able to understand how to woo and attract very quickly.  Some struggle.   I personally love it.

Simple dating tips applied to fundraising:

1. Communicate, proactively.  Communication in person > communication by phone > communication by email/text > no communication at all.  Laziness typically won't win.  Find enticing ways to meet in person.  
2. Don't talk too much.  Embrace silence.  Ask good questions.  Listen.  Give them opportunities to ask questions.  Observe the room (and yourself).  Manage the energy, not data points.
3. Be interesting, and be interested in your date.  Ask good questions.  Offer something funny or insightful.  Ask about their children or if they like the newest Tesla updates.
4. Be dependable.  Show up when and where you said you will.  And on time, if not EARLIER.  I've noticed most (good) investors are really good about that.  Remember important dates (birthdays, etc.).   
5. Be very responsive.  Lead if you can to set the rhythm of communication.  If the other person sends a communication, like an email, do everything you can to respond quickly (under 2 hours best, under 4 hours acceptable).  Demonstrate that they are VERY important to you.
6. Be polite and respectful.  Say please and thank you.  Follow up after your date to recap that you enjoyed the conversation.  See if there's interest in doing another date or keeping in touch.
7. Compliment.  Notice the details of the person(s) you are in pursuit of.  Notice if they like sports or whiskey.  Demonstrate you appreciate their feedback or opinions.  Give extra kudos when they say or do something awesome.  Read up on them and compliment them on their latest press/news.
8. Study them.  Do they like meeting up during the day or evening?  Are they casual or not?  Do they lean forward or are they more laid back?  Do they prefer coffee or a beer?  Does ambiance matter to them or is it all business?  
9. Figure out how you disagree.  The precedent set on how you handle conflict with each other is important.  See if there are some benign topics you can try out together.  There will be some micro-actions or non-actions that'll be good cues on how this will go.
10. Tell them directly you want them.  Pursue. Find the right method that will match what they will respond best to and tell them you're into them.  Really go for it and woo them.  Close the deal.  Don't beat around the bush.  Make the ask.

Maybe it's a stretch, the dating analogy.  Let me know what you think.
​--Arry

​Startup steam depletion.  I've been on the startup journey for a few years now.  Isn't that crazy? GiftStarter won 1st place from a Startup Weekend hackathon and then by July 2014, we were incorporated and diving into launching our MVP (Minimum Viable Product - we called it a Minimum Viable Experience, or MVE.) in August 2014.  

I'm standing now, with a totally different team, having depleted most of our steam - and figuring out how to keep going.  Because honestly, I've run out of steam.  We're going today mostly thanks to the heartfelt energy that came from Jin and Sean in the past 6 months.  

What happened between August 2014 and today (April 2017)?

2014:
From 1st place at a Startup Weekend hackathon, we moved forward.  I dove in, sprinting and grabbing every opportunity I saw to give us a chance.  Decisions were made very swiftly.  We launched as a B2B company.  Our initial model was focused on growing relationships with partners who were ecommerce businesses, that drove consumer traffic to our web application (that would enable people to group buy any product.)  Our goal was to sign on 10 businesses.  We signed on over 27 in less than 6 months.  Well, then the relationship with our co-founder/CTO ended very abruptly at the end of 2014.

2015:
Even with 27 ecommerce partners sending traffic our way - the referral business didn't pick up.  Our hypothesis was proven wrong.  The direct and consumer traffic was growing at a significantly faster rate.  Decision made again.  We switched to being a B2C company in May 2015.  We rebuilt a slightly better consumer site - and even did a v2 refresh.  Decision made to change out the team.  I hired a whole new team (also went to a remote work structure for the company when joining 500 Startups in San Francisco.  We were still CTO-less.  Being CTO-less was a bigger challenge to the company than I realized at the time.  My third co-founder also stepped out at this point to focus on family.  This is the also the story about me being the first pregnant CEO (8 months pregnant) to pitch at the 500Startups demo day on October 31, 2015.  We were the 7th fastest growing startup in our batch, gift transactions were growing 50% MoM.  We also raised about $500K for our seed round.  

2016:
I overestimated my abilities, overestimated the team I had, underestimated the magnitude of what being a first time mother would be like, and completely underestimated what it would take to run a fledgling startup company, with a remote team (and I can write more about to remote work as a company, or not later.  My vote is don't do it.  Remote workers care more about "me" than the "we".  A startup's life and death is all about "we".)  Hindsight, I should have asked for more help as soon as I found out we were pregnant.  Find an executive.  Actively look for that CTO.  Ask our investors for support.  Something.  I did the best we could.  Two weeks after the "Lentil" was born, I was back at work.  That didn't go so well.  At all.  I was like a crazy person.  I tried fundraising.  I don't recommend doing that after giving birth.  Giving birth to a human and all of the emotional, psychological, mental, hormonal, and physical aftermath is a really big deal.  We lost steam.  We ran out of money.  I even second mortgaged our house to carry us as long as we could.  Startup steam depletion.

Obviously, that was not sustainable.  Another challenging decision made finally.  I had to let go of all the employees.  With full on postpartum depression, my depression sank deeper and deeper.  I think I'm still working on recovering from depression.

Then at the end of the year, our current investors gave us some more funds to carry on and re-test the metrics we had achieved in 2015.  I cannot thank them enough for believing in us.  Then, we discovered some crazy new product/market insights that we need to think through and test further.  And...
  
2017:
Lots of fronts that need attention and decisions:  My baby is 14 months old and needs his momma. My husband is very busy with his job (and very supportive of me. Actually, the biggest supporter of me and our startup that I know of.)  Current investors continue to be very supportive.  And we are at startup steam depletion: of energy, funds, and people.  The market has changed a bit since 2015.  After 3+ years without earning a salary, I feel the need to start earning cash for my family.  The product needs a major upgrade.  In hindsight, I see some other items we should be doing.  We need to rethink our strategies and roadmap.  

So here we are.  (I'm really tired.) 

Now it's Arry + Sean left standing and rethinking through everything.  More than anything, I've discovered, startups are a HUGE mental game.  I feel like I'm a professional athlete competing in the Olympics.  

Mind over matter.  

Would appreciate any positive thoughts or support you can provide.  I need your help to keep going.   Many more decisions to make.  Fast.  

Thanks for reading.
--Arry

I see him every so once in awhile these days.  He's a wizard.  I hadn't seen him in a very long time, at least a year.  He asked, "so...  you're depressed.  You've been depressed for about a year and a half, huh?"  Funny thing is, yes, I have been depressed.  For that long.  I'm currently depressed.  My body aches and hurts, ALL THE TIME.  So much aching.  I've tried everything from massages to Advil.  I've even signed up to try acupuncture to stop the pain.  And yes, I definitely had postpartum depression.  It was really hard.  I wondered, "how did he know?"  Then he proceeded to stress that I start taking 5,000 IUs of Vitamin D3 asap.  ASAP.  Take it every day for two weeks and I'll see a difference he promised.  He insisted I walk across the street to Walgreens and pick some up right away.

​So I did.  

So today marks Day 1 --- I'll report back in two weeks (maybe before) on if I notice anything that I credit to the Vitamin D.  I want to feel well again.  

That's it for now.
Arry

Row, row, row your boat,
Gently down the stream
Merrily, merrily, merrily, merrily
Life is but a dream
[Full lyrics here]

(I am late to publish my #postaweek2017 for last week.)

In general, when it comes to life, the best way to live, is to not expend more energy than needed to accomplish a goal.  Rowing a boat against the current, or upstream is WAY HARDER, than just sitting in the boat and letting the river take you.  

This "Row, row, row your boat" thinking can be applied to:

• Career: There are rules to the game you're playing - know what those rules are and how it's being played before trying to change it and/or tell people what the rules should be.
• Sales: Don't go towards the people that have no interest in the problem you solve.  Go where people are looking for solutions, and your business makes sense for them.  This also applies to
• Fundraising (similar to sales): It's much easier to raise capital from folks who 1) understand the space you are in or the problem you are solving, 2) or who are interested in that space and want to expand their experience with you.
• Marketing (& sales): The idea that the "trend is your friend" is true.  If most businesses/people are working on figuring out a new trend in social media, trying to sell them large billboard signs (to throw an example out there) may be difficult.  Be where the market is and learn the distribution strategies to reach people where the people are.
• Building a team: Have people join the team that want to row with you, work shoulder to shoulder with you, follow you, grow/lead with you.  Getting people to work on things that only interest them because of the prestige or the money, will only motivate them for so long (or at all.)  
• Changing anything: When it comes to change, it's important to know what the current situation looks like.  Who are the key players?  Why does the current process, system, or anything exist the way it does?  What are the challenges?  What is the most important thing (MIT) of the people, process or systems that exist today.  Find out how to become or access the movers that MIT.  

Lately.  I have been applying the "Row, row, row your boat" principles to the topics that are coming up a lot lately in the ecosystems I am part of.  The topics of "Women in ___" (be it in the workplace, in tech, in startups, in leadership, in the C-Suite, etc...", and "Diversity" (be in race, gender, etc...).  My current belief is that we're missing a purposeful coordinated focus on identifying and influencing MIT in what'll really move the needle in a meaningful way.  That's why the whole topic of gender, of women in ___, of social equity and many similar topics have been so slow to change.  

Thoughts?

​--Arry