Heather Smith, Bill & Melinda Gates Foundation; Jess Stipe, Moz; Nicci Herron, Rover.com

Seattle Startup Week is a week long celebration of entrepreneurship in Seattle. On October 9, 2018 we hosted an event that focused on Executive Assistants with panels of EA’s from small startups to large tech companies. Those in the field know an executive assistant is the unsung hero of the office who is running the show. Executive assistants spend countless hours anticipating the needs and supporting their bosses to make the CEO look good and of course to keep him or her organized. Though there are endless professional development and conference options for any given profession, executive assistants don’t have much to depend on in this arena. Peter Chee, CEO and founder of thinkspace, and his EA, Stephanie Slaton, decided to take on the task of bringing together EA’s from all over the Seattle area and create the opportunity for a shared learning experience.

Leslie Hall, Amazon; Lynanne Lewis, Bill & Melinda Gates Foundation; Sheena McKinney, Heinz Marketing

The first two panels included amazing Executive Assistants from Amazon, Bill & Melinda Gates Foundation, Rover.com, Heinz Marketing, and Moz, and excitingly the final panel highlighted both the CEO and EA from Heinz Marketing, to capture how to best partner in this role.

We were able to transcribe Matt Heinz and Sheena McKinney’s responses to this final panel and have shared it below. Head over to the livestream links to all three of the panel discussions to hear more!

Video link to Panel 1 – Train Like the CEO/Executive That You Support
Video link to Panel 2 – Tips and Tools From the Best EA’s in Seattle
Video link to Panel 3 – How Best to Partner With Your EA

Matt Heinz & Sheena McKinney, Heinz Marketing; Stephanie Slaton & Peter Chee, thinkspace

The last panel showcased Matt Heinz, CEO of Heinz Marketing and Sheena McKinney, Executive Assistant to Matt. It was great to see the two of them on stage together, interacting, and communicating. They have been working together for four and half years so it was good see what a well-oiled machine looks like. Below are some of the questions that we asked them starting with a lightning round of questions:

Interview Lightning Round:

What is your favorite guilty pleasure TV show? 

Sheena: I watch a lot of HGTV and Food Network, but I must confess…. with emphasis on the word “guilty” vs. “favorite” … I watch The Bachelor.  I know.  It’s embarrassing.  My own brother almost disowned me when he heard I watched the show.

What do you think about when you’re alone in your car? 

Sheena: I’m pretty task oriented so I tend to think about things I need to do.  I press the home button on my mounted-hands-free iPhone and tell Siri “add eggs to my groceries list” or “remind me tomorrow at 10 o’clock to update the spreadsheet”.  I will also say– on the way to work I listen to the radio in my attempt to keep current and on the way home I listen to my book club books on Audible.

What is a hidden talent you have that has come in handy at work? 

Sheena: I find writing comes easily for me.  I’m able to send off emails without too much thought and occasionally I get to write blog posts for our blog.

Best Partnering Questions:

First, how long have you been working together?  4 ½ years

Matt, one of the key reasons Peter was hiring an EA was to open up time, 5 hours a week specifically. What are your top reasons for hiring an EA and how has hired Sheena changed the way you work?

Matt: Having a great executive assistant can make you literally 3-5X more productive than you can be on your own.  It’s not just taking stuff off your plate, it’s delegating those things and having them done better, faster, smarter.  And when I focus on the right things, it has an exponential impact on my business.

What are your work styles and how do you compliment one another? 


    • We are both zero inbox people.  I’m so addicted to the freedom of this approach I’m also a zero-saved-texts person. Anything I might need from a text I copy/paste/save elsewhere. For sentimental conversations like a mushy note from my husband or a screen full of emojis from my granddaughter, I take a screenshot and save it to my photos.
    • The way we approach tasks and information is very similar.  Matt is a David Allen “Getting Things Done (GTD) guy and I originally learned the Franklin Covey system back in the early 1990’s (when Matt was about 14 years old— which makes me feel really old!).  There are a lot of similarities, especially in GTD’s Five basic steps.
    • I’m naturally more here/now minded and less future minded.  Matt’s really good at short, mid, and long term planning and goals so I think we compliment each other here.
    • I’m more detail oriented (not that Matt isn’t).
    • I have perfectionistic tendencies… Matt is better and letting “Good” be “Good Enough”
    • He works better in the morning, I work better in the afternoon

Matt: Before we hired Sheena, our HR consultant told me I needed to find someone who would take an assignment and think through the next 4-5 steps to get it done (vs me having to telegraph it).  Sheena does that really well and isn’t afraid to come back to ask for further detail.

We also have our own hidden language of sorts.  For example, I’ll reply to someone telling them I’m happy to grab an intro call with them and copy Sheena.  Sheena knows that means a 30-minute call, knows when during the day to avoid scheduling it, etc.  These levels of efficiency take time but they add to the extreme benefit of having an EA.

Expectations are important and communication is key. As the Executive Assistant, how do you set expectations with Matt? How does he set expectations with you?  

Sheena: Yes, communication is key and we are in almost constant email communication.  Our weekly 1:1 meeting is also a key way to set and communicate expectations.  Sometimes, we’ll email each other prior to our meeting when the list is longer and/or needs some previous thought or research.  Our annual review is really helpful in setting goals and areas of improvement.

How do you decide when it’s appropriate to use “short but sweet” communication vs. detailed communication? 

The key word here is “decide” I naturally lean toward too much detail but I’ve learned to be as succinct and concise as possible at all times– because of whom I married and because most of the exec’s (current one included) strongly prefer “short but sweet”.  I sometimes (literally) will reply to an email with “Short Story:……….and list the info. with bold fonts, underlines, highlights, etc. and below that, “Long Story:…. And then list out all the detail and back story… knowing full well he may not read it… but it makes me feel better and in some cases, if he questions the short answer… the longer one will help him understand why I arrived at my conclusion/decision.

How do you know when to solve a problem on your own or to ask for help?

Sheena: Plan A is to always try to solve the problem. 1.) I have self-sufficiency issues, 2.) It’s my job to gate keep and let Matt do what he does best.  If it’s a completely new issue where I do not have previous experience from which to draw, I’ll ask for help… sometimes from one of our VP’s who has been around longer and knows Matt and our business better.  If the outcome of the problem could negatively reflect on Matt and/or Heinz Marketing, I will ask for help because I/we care about integrity a lot and I’d rather be safe than sorry.  Fortunately Matt is good and quick at making decisions and is so approachable I feel pretty free in asking when I do need to ask for help.

What have you found to be the most effective way to work together?

Sheena: Open, continual communication is key.  I truly want feedback, the good, the bad, and the ugly. We’re both comfortable with fierce conversations.  Also believing and assuming the best is important. Mutual respect and expressing appreciation is crucial.  At a previous job I had no idea how I stood with my boss.  It wasn’t until months into the job at the company Christmas party (and the alcohol was flowing) I found out from my co-workers how much my boss appreciated me and was glad he hired me. Matt does a great job of showing appreciation and confidence in me and that’s priceless.

We have startup founders and CEOs in the crowd today too, what advice can you give about how to hire and onboard your EA. 

Matt: Do what I did, start the week by making a list of all the things you do that someone else could do for you.  Next to that write how long it took.  At the end of the day look at how many things and how much time is reflected, and consider the opportunity cost of what you could have spent that time doing.  It won’t take you long to do the math and start the hiring process!

grit-resilience-400-katie-walvatne-granite-mountainMy whole life, I’ve recognized that I’m not the smartest person in the room. There are always people that are smarter than me. I’ve had to work twice as hard as the other person in order to get the same results. When I was really young, I watched how a tennis player, Michael Chang, show tremendous grit and battled back through one of the most grueling matches against the number one player in the world. From that moment, my mind was made up that no matter what the challenge, I would find a way to out last it and if I’m going down, I’m going down swinging.

“Grit is passion and perseverance for especially long-term goals.” – Angela Duckworth

Between 2008 and 2011, I survived one of the most difficult and stressful times of my life. With a young family of three toddlers I put everything on the line. All-in, as defined by all my personal financial resources, all my emotional energy, heart and soul, everything at risk to start up my company and survive a startup company in a recession. On top of all that, I had a period of 770 consecutive days where the bank called my loan and asked me to repay a million dollars. For me, that’s not something I can find in between the sofa cushions. It was through massive struggle that I was able to solve that issue and actually not go bankrupt.

“Big smarts with medium grit tend to loose out to medium smarts with big grit.” – Martin Tobias

After surviving that, I knew that I wanted to increase my margins. Margin is the space between your load and your limits. I wanted to push the edge out further. I don’t want to ever feel like I’m about to fall off the edge. One thing I did to reduce my stress was start running, I ran a couple half marathons which helped me train to manage my stress and keep me from physically tipping over.

Push the Edge Further Out

Life hits hard. In a period of one year, three people I knew between the ages of 25 and 40 passed away from cancer. Life can hit you so hard and it will keep you down if you let it. I vividly remember the feeling as I walked step-by-step with Shonda, a friend and employee, as she battled through nine months of fighting cancer. After a few months of reflecting, I decided to run a marathon, which would help me push the edge out further so that I might have a fighting chance to get through what random things life throws my direction. I believe that most things in life you can figure out if you have enough time. Staying upright on your feet is part of the battle and that’s done by being physically strong so that your mind can figure out how to break through!

Resilience is About How You Recharge, Not How You Endure

Resilience: The capacity to recover quickly from difficulties; toughness. – Merriam-Webster

Maybe I’ve seen too many Rocky Balboa movies and the picture of resilience is when Ivan Drago says to Rocky “I must break you” and they go on to exchange body blow after body blow. Resilience seems to be confused with grit, that the longer you can out last someone the more resilient you are. It’s like you have to be able to pick yourself off the turf for one more play. What if that’s not what resilience is at all?

The key to resilience is trying really hard, then stopping, recovering, and then trying again. – Shawn Achor and Michelle Gielan

Upon reading the article “Resilience Is About How You Recharge, Not How You Endure”. I found a few quotes in there that talked about:

“If you spend too much time in the performance zone, you need more time in the recovery zone.”

“That if you want to build resilience, you start by strategically stopping. Give yourself the resources to be tough by creating internal and external recovery periods.”

When early on in my entrepreneurial journey, I read entrepreneurship is living a few years of your life like most people won’t. So that you can spend the rest of your life like most people can’t. Parts of this are very true for me and other parts I’m still figuring out! I’m also still looking at the word resilience and trying to see how much of that I have.

If you’re looking for answers to know whether or not you have Grit and Resilience, register for our event at Seattle Startup Week. Space is limited as we deep dive into this topic:

Grit and Resilience: Do you have what it takes?
Date: November 17 @ 1PM
Location: Google Seattle

Before you attend the event you can also take Martin Tobias’ Grit Test to see where you land on the Grit Scale.

Martin Tobias, Serial Entrepreneur, Investor, Founder, MGT Investments
Anne-Marie Faiola, Founder and CEO, Bramble Berry
Matt Williams, CEO of Pro.com
Peter Chee, Founder and CEO, thinkspace

Other sources:
If you’re looking for some good talks on Grit, watch Angela Duckworth’s TED Talk. Angela also did a talk at Google called “Grit: The Power of Passion and Perseverance” which I found to be even better as it relates tech companies and the startup mindset.

dark-side-entrepreneurship-posterThere are a lot of positives of being an entrepreneur, but, we’re going to get raw and talk about the dark side of entrepreneurship.

Over the last couple years there’s been more transparency on the topic of what the “Darkness of Entrepreneurship” really is. Rand Fishkin, founder of Moz.com, describes what it can really look like in a epic blog post that he wrote: “A Long, Ugly Year of Depression That’s Finally Fading”.

As an entrepreneur you will face a lot of painful things like fear of missing payroll, not spending time with people you care about as you work 80 hours a week, the highs and lows within the same work day that make you look bi-polar, the stress eating or bad eating habits, and struggle raising money from investors. During Seattle Startup Week our event on The Dark Side starts here and goes beyond that.

The dark side is what’s on the other side of when your trajectory is going great, you’re hitting your revenue goals, and your company is being recognized as one of PSBJ’s Fastest Growing Companies for a couple years in a row as the company is growing at 90% year over year. But as you try to execute and fail to continue the growth you feel like you’re making bad decision after bad decision. You lose key employees and you question your ability to lead. Your key investor, points a finger at you and says to you, you made all these hiring decisions. You have no choice but to own it. It hits you that you’re no longer enjoying any of the work that you used to enjoy. You ask yourself questions like did I just make one of the biggest mistakes of my life and spend years investing all financial and emotional resources into something that is failing? These are the things that cause you to lose sleep, gives you shortness of breath, as you cry yourself to sleep. Maybe some of you know what I’m talking about?

This event is going to talk about some of these challenges and some of the things that entrepreneurs have done to cope, survive, and find clarity in these kinds of times.

Register here: The Dark Side of Entrepreneurship: What No One is Talking About.
Date: November 16 at 12PM

Martin Tobias, Founder and Investor, MGT Investments
Jesse Proudman, Distinguished Engineer and CTO, IBM Blue Box
Jen Mueller, Founder, Talk Sporty to Me / Seahawks Reporter
Michelle Hollomon, Coach and Counselor, MA, LMHC, CPC

Talk Sporty to MeSeattle Startup Week kicks off November 14th with an event focused on “The Intersection of Sports and Startups“. We have Jen Mueller, founder of Talk Sporty to Me and Seahawks Sideline Reporter moderating the event. Jen is also the author of the book “Talk Sporty to Me: Thinking Outside The Box Scores”. Here’s a little bit about the book:

Any book that starts with a paragraph about the Seattle Seahawks winning the Super Bowl against Denver is going to be a great book! The parts that I liked most about this book were quotes from various people in Seattle like Coach Pete Carroll and his philosophy to “Always compete”. I also really enjoyed the conversation that Jen had with John Nordstrom when he talked about three things 1) “Everyone is included” 2) “No one wants to take credit for any of the success” 3) “Pete (Carroll) understands the importance of the last three feet”. The last three feet, refers to the distance between you and the customer. In my mind it also refers to the last yard in a startup where you need to make sure the customer experience is great or it could also be the final yard that propels you forward in your startup.

Sports is a great way to get a conversation going and build rapport with people. This book is useful for anyone starting out in the business world or branching out into a new industry that wants to understand how sports can be one of the ways to create a connection with someone.

Space is limited at the Seattle Startup Week event, please be sure to register for “The Intersection of Sports and Startups“.

Jen Mueller, Founder of Talk Sporty to Me and Sideline Reporter for the Seahawks

Speaker Panel:
Chuck Frizelle, CEO of Coros
Jesse Smith, Manager of Analytics for the Seattle Mariners
Josh Decker, CEO of Tagboard
Steve Schwartz, Founder of ProInfluence

code-fellows-ssw-sponsor-logosCode Fellows, a Seattle Startup Week sponsor, is a code school training both mobile and web developers in industry practices, in-demand frameworks and technologies.

What makes you excited about Seattle Startup Week?

A chance to connect with all of the resources that happen over a year in one week.

What are you hoping to get out of the week of events?

Awareness of Code Fellows with a broader community of potential co-founders and future employers.

What do you love about being part of the Seattle startup culture?

It has changed a lot over the years.  It’s great that we now have an ecosystem that is helping new folks get connected with resources.

If Code Fellows was a food, what would it be and why?

Spicy Mexican.  It’s something you expect, but it has a bit of a kick to it.

Hired LogoHired, a two-sided recruiting marketplace and a Seattle Startup Week sponsor, is on a mission to make both finding a job and finding quality employees easier.

What makes you excited about Seattle Startup Week?

We’re excited to support and participate in Seattle’s startup community.  In particular, we are excited to discover new companies, share ideas and meet interesting people.

What are you hoping to get out of the week of events?

We are hoping to be a resource for job seekers and to build partnerships with startups to help grow their teams.

What do you love about being part of the Seattle startup culture?

The Seattle startup culture is extremely welcoming and extremely innovative.  The people here are passionate about what they do and it shows in their enthusiasm to help others and give back to the community.

If Hired was a food, what would it be and why?

Hired would be a Vegas seafood buffet.  It serves and satisfies everyone and is a pleasure to experience.

Fremont Run To Beat Breast Cancer LogoSeattle Startup Week is only two weeks away, and preparations are in full swing here at thinkspace!  October is also Breast Cancer Awareness Month.  And you know we are always looking for ways to build and strengthen our ties within the community. If you’re a part of the startup community and we haven’t met you yet, we’re hoping to change that soon.  And if we have already met you, we’d love to see you, too!

We’d like to invite you to spend your morning with us on Wednesday, October 28th for a 5K Run to Beat Breast Cancer.  Run, walk, skip, jump and be merry with us.  The run begins at 8:30 am and will take us along the Burke-Gilman Trail and through Gasworks Park.  Stick around after the run concludes to eat some breakfast noms and jam out to some early morning disco tunes at our Fremont location.

The event is free, but we’d appreciate any donations you can put forth.  All proceeds will go to raise funds for Dr. V.K. Gadi’s research at Fred Hutchinson Medical Research Center.  5K t-shirts will also be available for $20, with all proceeds supporting Dr. Gadi and his team.

RSVP for the Fremont Run to Beat Breast Cancer here.


Peter Chee, Ali Spain and Katie Walvatne at Brunch to End Breast Cancer October 11, 2015

Can’t make it on the 28th?  Running just isn’t your thing?  Not to worry!  We’ll be supporting Breast Cancer Awareness Month throughout Seattle Startup Week, with opportunities to make a donation to the Fred Hutch team at each of our events:



Name.com logoName.com is a domain name registrar, web hosting company and a Seattle Startup Week sponsor.  To get to know them a little better, we asked them a few questions.

What makes you excited about Seattle Startup Week?

We are excited to support Seattle Startup Week because we love the whole Startup Week movement.  We’ve supported Boulder and Portland this year too, but see a particular energy in Seattle’s startup scene that’s infectious; and we want to be a part of it.

What are you hoping to get out of the week of events?

We are hoping to spread the word that new alternatives to .com domains are now available.  Domain name extensions like .ninja, .social, .news, and 1,300 others are becoming available.  We love these names because they inspire people to come up with new ideas and discover new possibilities on the Internet.

What do you love about being part of the Seattle startup culture?

Our favorite part of the Seattle startup scene is the drive that people have.  There’s a unique sense of “anything is possible” in the Seattle area.

If Name.com was a food, what would it be and why?

We would probably be lasagne.  That’s because we are simple on the outside, but super complex on the inside.

[sched sidebar=”yes” url=”http://seattlestartupweek2015.sched.org/”]Seattle Startup Week Schedule[/sched]

andy-presentingBy 1:00 pm on October 23, the day of his Seattle Startup Week presentation, Andy Liu, local dream investor and CEO of BuddyTV, had already been in contact with four prospective customers. According to Andy, his number one job is to sell.

“You know what? As CEO, sales is actually my number one job. Sales to customers, sales to employees, sales to investors…Sales to everybody else that may eventually come into contact with the company…I need to constantly be doing that.”

Getting in front of the customer is one of the best ways to learn about a business.

Andy also explained that businesses are built on rhythms. Therefore, it’s crucial that a company reevaluate the rhythms that are in place to be more effective on a day-to-day basis. To do this, Andy has implemented a number of rhythm-boosting practices. For example, every Monday morning he sends out an email to the entire team with BuddyTV’s latest happenings, team recognition, and any other relevant information for the upcoming week. Another tool he uses is a refined system of key performance indicators.

“It’s not 30 numbers that you need to track, it’s one or two.”

Andy wrapped up by highlighting the importance of celebrating.

“Even in the darkest days, there’s always something to celebrate…There’s always some reason to ring the bell.”

Andy follows his own advice quite literally. In BuddyTV’s office, one of the developers has a cash register linked up his computer speakers. Each time a sale comes in, the cash register dings.

What does your startup do to celebrate?

You can hear more about Andy’s rythmatic practices here:

Check out Andy’s SlideShare deck from his Seattle Startup Week presentation:

Or see the entirety of Andy’s talk here:

Check out our recaps of our other Startup Week events:

Kicking off with Aviel Ginzburg of Simply Measured
Matt Heinz explains why you have to fail in order to succeed
Russell Benaroya talks night runs and how to ease the loneliness of entrepreneurship