A thing I have noticed, after a LOT of experience on this since my early childhood days, is that opportunities show up all the time. I notice the opportunities some of the time. I take the opportunity even less times. And many times, when I do notice the opportunity and decide to take it - it's very often NOT when I was wanting to do that sort of "changing of plans".
I've also noticed that being an entrepreneur, and in the field of startups, a key skill that a founder really needs to have is the ability to listen/observe, and make a decision to act or not act, fast. There's a saying, "time kills all deals". Time can kill opportunities if you take too long to make the decision.
And the third thing I've noticed, at least for myself, is that when I have that mix: 1) an opportunity, 2) that I notice, and that 3) I decide to take it PLUS I feel that familiar pang of discomfort, I know i have to jump all in and fast. Go where I can sharpen my edges like the sword of a world class warrior All hands on deck. I start moving and I figure the rest out as I go. Pangs of discomfort, the anxiety, the sweaty armpits and knots in my abdomen keeping me up at time running through all the possible scenarios - especially the worst case scenarios where I get beaten emotionally, mentally, physically, and ... the fear of failure is real. So real. I feel that worry of what if I am an imposter. What if I actually know NOTHING. What if I'm actually completely incompetent, ineffective, and a total fraud. My worst fears.
I hold them to be possibilities that may be true.
Time does kill all deals and so I take all of my fears, my worries of embarrassment, and my battered bruised beaten self and I get into position to fight again. I may be battered, bruised and beaten - I've also built up some gnarly badass wise scars, and some dense diesel muscles that can fight better than some of the best.
More to come.
This past week was interesting. Last year, my husband and I, after years of playing "secret investor" by ourselves practicing which ones should or shouldn't or rather would or wouldn't raise the funding that they "needed", we finally started really investing real dollars. Small checks. Putting the walk to all our talk to see if we really had some useful insights into investing in startups. We think we do after being in the trenches of GiftStarter (my intra-preneur experiences plus my husband has also led a series of other small retail businesses), so we shall see.
Anyways, one of the founders we invested in needed some help with their pitch, and I helped as best I could (shaking everything I knew about fundraising and good pitch presentations). They needed help with their pitch deck, so I rolled up my sleeves Sunday night and burned the midnight oil "beautifying" the pitch deck in PowerPoint. The founders needed help with their financials, so I created a customized financial plan template that would help them navigate their projections. Then it looked like there would be 3-4 investors in the same room during one of their pitches, ... and given the situation, I figured I could fly in/out the same day to be another pair of eyes/ears in the room - so I agreed to fly to SFO the next day. Anything that I could possibly do to give them a chance, a leg up at success.
When I think about it, having that "lift" available from someone who's well-rounded, another entrepreneur/founder/CEO person who's been through it as guidance for your company, whether it be an advisor, mentor or investor is REALLY HUGE. Most advisors, mentors, investors ---> they try to help sometimes, they will write checks or spend an hour or few here and there.... but most of the time, they really don't have the 1) founder/entrepreneur experience, nor the 2) founder/entrepreneur "brain" on doing continuous critical thinking to actually provide any meaningful value. I guess, we figured, that's the real value we (myself, and my husband) can provide - the real founder/entrepreneur experience to help another founder/entrepreneur save time and energy in this journey.
I learned to play poker almost a decade ago through a Seattle startup connector called Startup Haven that connects founders with education, opportunities and (most importantly) each other. Through this journey that began in 2008, I have learned that there are a lot of similarities between the startup world and the game of poker. I have even found myself making references to poker moves in my role as a founder and CEO.
Through this journey, I have learned that there are a lot of similarities between the world of startups and the game of poker. I often find myself making references to poker game moves a lot. For example, do I fold or raise on the consumer side of our business? Do I double down or raise when it comes to employees? I even know to play aggressively when I see a possible win on the other end.
The photo below is a photo of me winning my very first poker game (out of 50-ish people) in January of this year. Crazy. BTW, if you are a startup founder, I definitely recommend checking out Startup Haven and playing the Poker 2.0 games. Super fun. You don't have to know how to play poker to go.
Last week, we had Phil Gordon in to play with us. Phil Gordon is a professional poker player who has placed multiple times in the World Series of Poker – a big deal. He’s been a commentator on poker games, designed digital poker games, and written several best sellers on poker. But more importantly, Phil is also an entrepreneur.
Before we started playing, Phil took some time to share some insights that would inspire us founders at the table: eight startup lessons we can learn from poker:
If you were to relate your startup journey to a poker tournament, where would you be right now? What does your hand look like? Are you being aggressive or not?
If you’re to take any entrepreneurial lesson from poker, it’s to be real. Don’t talk yourself into playing if you don’t know that you have the best hand. How you get to the end does matter. Don’t sell yourself short by running out of fuel earlier than you want.
I got a photo with Phil. Neither of us won the poker game in February 2017. :)
PS This article was originally posted here.
Still doing the Vitamin D therapy every day. Eat dinner. Pop in vitamins after. That's been our routine for about 40 days (I fell off this routine on about day 41).
The Vitamin D Report:
Summary? I'm a believer. I believe the vitamin D3 therapy did actually work and pull me out of the dark part of the depression I had been wallowing in for some time.
No assholes allowed.
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:
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.
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:
Maybe it's a stretch, the dating analogy. Let me know what you think.
Running out of steam
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)?
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.
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.
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...
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.
I saw my "coach" yesterday.
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.
Row, row, row your boat
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:
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.
Motherhood is hard. There's so many changes that I've gone through to list, and while not everyone has the same experiences, here are mine (not in any particular order of importance).
Motherhood is hard:
Often, I'll share and say something like, "wow, motherhood is hard". You learn a lot about who people are with the responses. Now having been in this for over a year, I've noticed a most definite pattern. I will always get one of two responses to that question. They go something like this:
Supportive fellow human being:
A) Yes. My gosh I can (or cannot) imagine. With the follow up of, let's go grab some coffee or I'd love to share more with you on this journey. I want to show you that you are not alone and I am here to feel shoulder-to-shoulder in life with you. I want you to know that it'll be okay.
Judging oppressive human being:
B) Of course it is. And, isn't motherhood the most rewarding thing you've ever done? Isn't it completely and totally worth it? There's only one right answer here and you better say it. Motherhood is amazing and that's the only thing any mother should ever say. Ever. Because it is completely worth it.
We get to be the guardian of a brand new fresh pure amazing human life, to guide him (or her) to grow up to be a kind, generous, strong, empathetic, respectful and respected adult. It is hard work. Both ideas can exist.