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Life

Happy 100th Birthday Grandma

By Life
Ann Bea Maloy at her 90th birthday party. I love this picture because she was so pleased with having a tiara for the day. Seeing her joy and energy at 90 makes me smile & laugh every time I see this photo.

Today, 4/17/2020 my Grandma (my dad’s mother) would have turned 100. I grew up half a mile from her and my grandfather in the house that they bought in 1948, and owned until she passed away. She was a big part of my life growing up. During high school I spent nearly every Sunday afternoon over there talking with her and Granddad. We had chipped ham sandwiches (it’s a Pittsburgh thing) and “Grandma’s Iced Tea.”

Her iced tea was famous—it is the sweetest sweet tea you’ve ever had. I’ll make you some when you come to Colorado. She had to make gallons of it for every family gathering because we all loved it so much. 

She was an amazing woman that showed love, kindness and understanding to all of her children and grandchildren. Some highlights about Ann Bea Maloy include: 

  • Earned her bachelor’s degree from Pitt when few women went to college
  • Her best friend was Jewish (this was unheard of, on both sides, for her generation) 
  • A savvy investor who understood the time value of money
  • A lead foot driver who used her white hair as a tactic to merge at the very front of the traffic
  • Doted on her grandchildren through her whole life 
  • Loved big gaudy jewelry
  • Always said, “we Irish need to stick together”
  • An independent woman, growing old was hard for her because everyone always wanted to do things for her!
  • And she was truly the matriarch of the Maloy family 

To celebrate her life, we got together today for a family Zoom call and did an iced tea toast. My uncle put picture of her at 20 years old in the frame of his computer. 

Iced Tea Toast 4/17/2020

Happy birthday Grandma. Thank you for all you did for us, for all you gave to us, and for always being there for us. I love you.

What’s In There? Only What You Take With You.

By Life

Master Yoda

During the Dagobah scenes in “The Empire Strikes Back,” Master Yoda shares a lot of wisdom with Luke Skywalker. We all know the most famous, “Do or do not. There is no try.” It’s so deeply ingrained in our culture—especially startup culture—that it brings on ennui for me. It’s such a well-worn path that it hardly bears repeating.

There’s another interaction between Luke and Yoda that I prefer for its depth and multiple layers of meaning.

Scene: Luke stops deep in the jungle, and sensing darkness emanating from a nearby cave, he turns to Yoda.  

Luke: What’s in there?

Yoda: Only what you take with you.

Take a moment to reflect on that:

What’s in there?
Only what you take with you.

In literature and in Star Wars, the cave is a metaphor for a journey inward.

The Dark Side Cave

What’s In There?

Luke didn’t know what was in there, but he went in regardless. He brought in his fear and anger, and that is what he faced.

We go into every day not knowing what lays ahead. Sure, we have our calendars organized, and know where our lunch meeting is, and who to expect at the client meeting. And we know what we can reasonably expect when we go home. But we don’t really know what’s in there, be it on the road, in a meeting, or at home.

We don’t know, because “knowing”  implies certainty. We know precisely when the sun will rise for any particular point on the earth on any particular day. But we don’t know if our lunch meeting is going to happen, if the client meeting will go smoothly, nor if we will close that deal.

What’s in there? We don’t really know. But we go regardless.

Only What You Take With You

Luke was arguably not ready to face his dark side, but that cave—that challenge—was on the path of his training. What he found was what he took with him: his anger and his fear.

As we move through life, facing challenges, enjoying moments, getting excited, or being calm, how we are in that moment depends on what we take with us. Did you get blindsided by a difficult conversation? You faced it with only what you took with you. Did you prepare for the meeting? You faced it with only what you took with you. Each day we have new caves to enter with unknown challenges to face, and we do so with only what we take with us.

That is the unspoken layer of this dialog that I love so much: if the only thing in each cave—each challenge—is what we bring with us, then we should strive to bring the best with us at all times. This requires both self-awareness and training.

What You Have

In Star Wars, the ability to tap into the Force is innate; you either have it or you don’t. Luke brought his emotions and his abilities into the cave, just as we bring our emotions and abilities into each encounter. What do you bring to each challenge?

  • What’s in [today]?
    • Are you prepared for the day, coming in refreshed with a good mindset, or are you tired, frazzled and scattered?
    • Only what you take with you.
  • What’s in [your role at work]?
    • Are you adding value, moving things ahead, and keeping your mind & skills sharp?
    • Only what you take with you.
  • What’s in [your relationships]?
    • Are you bringing empathy and compassion into your relationship, or conflict and unresolved emotions?
    • Only what you take with you.

This ties into my Rule #6, “YOU are responsible for creating the world you want to live in.” Do you bring a lousy attitude, distrust, and anger into your world? Wondering why there’s only bad attitudes, distrust and anger facing you every day? It’s what you bring with you. What do you want the world to be? Bring that with you.

What You Can Train

Sometimes what we bring with us isn’t enough. Luke was in the Dagobah swamps to receive Jedi training from the only living master. We are fortunate we have many masters to learn from in our world. We need to train ourselves, or “sharpen the saw” as Stephen Covey says in his classic, “The Seven Habits of Highly Successful People.”

For example, in a professional environment when there are difficult conversations I need to lead, I spend hours preparing, rehearsing, and getting comfortable with what I need to say and how I want to say it. When I go into that encounter, what I bring with me is a prepared and ready mind. I’ve trained to lead difficult conversations.

To take more with you into each challenge, you must train.

At SpringTime I have much to learn; a lot of training ahead of me. We’re fortunate to have a team with diverse and complimentary skill sets, and we can all learn from each other. In addition, I read blog posts, listen to podcasts, read books (on Audible), and reflect on the lessons.

As a new father, I have many, many years of training ahead of me. There are many challenges to face, some I’ll be prepared for, and most I probably won’t! I read, learn, and reflect to continue my training. With each challenge, what I take with me enables me to be the best possible father to my son and soon-to-be-born daughter.

If we didn’t learn, grow, and evolve as individuals, we would live in a world of screaming infants—whether you want to take that literally or metaphorically is up to you.

Your weapons…

Your Weapons, You Will Not Need Them

Like Luke, I put on my weapon belt. But Master Yoda’s point is that it’s not about the tools on our belt, it’s about our mind and our preparedness. Regardless if I live by my Google calendar, keep all my to do’s in Trello, and take great notes in Evernote, none of it matters compared to what’s in my head.

I know that with each challenge, what I face it with is only what I take with me.

Ride the Wave to Shore

By Life

I should have been a surfer. In another life, I was born on the beach and grew up surfing, with a surfer’s philosophy ingrained into my being.

One of my rules is, “Ride the wave to shore.” I can remember when I first put this in writing, I was sending an email to someone on AOL—probably around 1999. I don’t remember the specific situation, but the context was about seeing something through and enjoying the journey along the way. I’ve ascribed to this philosophy for a long time.

Riding to Shore

On Thursday, my team and I were laid off, as well as nearly the entire organization that supported IBM’s Global Entrepreneur program. I got the news on Thursday morning, and then had calls to inform my team throughout the day. It may sound awful, but frankly, we knew it was coming; it was only a matter of when. One person even responded by saying, “oh that’s happening today? I thought it would be Monday.”

I believe in riding a wave to shore. Sometimes it’s the wave I meant to catch, sometimes it’s a different one. Sometimes it’s everything I thought it would be (and more), and sometimes it’s a let down. Sometimes, I get thrown from the wave before I can take it all the way in. But no matter what, it’s the wave I’m on, and taking it all the way to shore is the best way to get the most out of the experience.

In 2012, I was a part of a startup that was in the SoftLayer Catalyst program, receiving credits for servers, plus mentorship and connections from Josh Krammes and his team. Later, I joined the  SoftLayer Catalyst team as a Community Manager in 2014, covering the Rockies region, and soon began covering everything from Portland to Pittsburgh. In 2015 I took over managing the US & Canada team. I hired a number of people, lost some good ones to attrition, and built out a well-rounded group. In 2016 we fully integrated into IBM and became the Global Entrepreneur program. And in 2017, the whole team was laid off.

I can truly say, I rode my wave right down to the shoreline. Now it’s time to paddle out and catch the next one.

Paddling Out

If you’ve never surfed, then you don’t know the least sexy, rarely shown, and most frustrating part of the sport: paddling out. Waves crash over you, you duck-dive under them, then frantically paddle with your arms and pathetically kick your feet, duck-dive another wave, paddle harder, and paddle and dive, and paddle and dive, and then look back, and it feels like you’ve barely moved at all. The hardest part is the very end where the waves start to break, the undertow is the strongest, and if feels like you’ll never get past it. You’re choking down seawater, barely holding on to your board, and then with one last dive… you’re through! Past the breaks, you can take a breath and float peacefully on the rolling waves of the sea.

Despite my longing to be a surfer, I have actually tried it a few times: in Bali, Indonesia and Ditch Plains, NY. In my brief experiences, I can tell you this: paddling out is hard work. There’s a reason you don’t see overweight surfers.

I rode this wave to shore, and now I get to decide if I want to paddle out in IBM’s waters again, or in someone else’s.

There is an opportunity to paddle out inside of IBM again, and it’s one that would enable me to continue to fulfill my personal mission: to transform the world through innovation and entrepreneurship. To make a move internally is not impossible, but it is work. It’s the unsexy sort of work that requires determination and a some convincing. Waves of doubt crash over you, as you paddle out through familiar, but different waters. Waves of fear crash over you as you put yourself on the line, opening yourself up to rejection.

Through it all, you have to keep your eyes on the prize (another one of my rules) and do the hard work that’s required to catch the next wave.

Everyone Needs a GSD Day

By Life

Time is Precious. Free stock photo from Harry Sandhu found on Negativespce.co

It’s Thursday night. My son is fast asleep. My wife and I are full from a delicious dinner. I feel totally relaxed, satisfied with a good day of work behind me, and ready for a strong close to the week tomorrow. I feel this way because Thursdays are my Get $#!t Done Days. And I did just that.

I have a recurring appointment in my calendar that blocks out every Thursday from 8:00 AM to 6:00 PM. I will take one in-person appointment, usually lunch—though today it was coffee—and that’s it. Otherwise, I don’t take any meetings, phone calls, or other appointments. I don’t schedule anything except time to stand at my desk and get. shit. done.

It takes more than just blocking off the time, though. Believe me, it is all too easy to simply accept calendar invites, or schedule meetings over top of the blocked time. I’ll admit to breaking my rule on occasion. Soon one call leads to two, two to three, and before I know it, my morning is gone in a blur of phone & video calls. By then it’s just another day, and I’m scrambling to stay ahead of the ever-mounting tide of work.

Respecting the blocked-off time is just as, if not more, important than blocking it.

With a full day of uninterrupted work ahead of me, it’s the perfect opportunity to tackle the things that require more than 20 minutes of attention. For example, today I spent one and a half hours working on a document for a big project. I was able to get into a flow state with my writing and analysis. If I was trying to hack at this throughout any other day, in between meetings, and in 20 to 40 minute chunks, it would have taken three times as long. Instead, I knew I had my GSD Day, so I kept a scratch pad of notes throughout the week and dove in deep today.

It felt great to knock out something important but not urgent.

Time-blocking is not revolutionary. You’ve probably heard it mentioned in one productivity course or another. I first learned it when I was starting out in sales at Robert Half Technology in 2004, and continue to practice it today. When things get crazy in the startup community, and my team is feeling overwhelmed, we talk about time blocking to ensure the work is getting done, and we’re staying sane.

I have other time blocks, too. Monday’s are my phone call days. I try to pack every single call into Monday; I’ve had many Monday’s with double-digit calls scheduled. Wednesday afternoons I block off to work from home so my wife can go to a yoga class she loves. I sit on the floor with our five-month-old son with my laptop open ready to hand him teething toys. But Thursday are the most important for my work and my sanity.

If you are in a job that pulls you in a lot of directions, schedule a GSD Day. Start time blocking to help yourself get ahead of the tide, and feel better about the quality of your work.

A Grandmother’s Advice for Startups: You Never Know Unless You Ask

By Life

Originally posted on the SoftLayer Blog on April 17, 2015.

Today my grandmother turns 95. She’s in amazing shape for someone who’s nearly a century old. She drives herself around, does her own grocery shopping, and still goes to the beauty parlor every other week to get her hair set.

Growing up less than a mile from her and my granddad, we spent a lot of time with them over the years. Of all of the support, comfort, and wisdom they imparted to me over that time, one piece of advice from my grandmother has stood the test of time. No matter where I was in the world, or what I was doing, it has been relevant and helpful. That advice is:

You never know ‘til you ask.

Simple and powerful, it has guided me throughout my life. Here are some ways you can put this to work for you.

Ask for the Introduction
Whether you’re fundraising, hiring, selling, or just looking for feedback, you need to expand your network to reach the right people. The best way to do this is through strategic introductions. In theCatalyst program, making connections is part of our offering to companies. Introductions are such a regular part of my work in the startup community. In my experience, people want to help other people, so as long as you’re not taking advantage of it, ask for introductions. You’re likely to get a nice warm introduction, which can lead to a meeting.

Ask for the Meeting
Now that you have that introduction, ask for a meeting with a purpose in mind. Even if you don’t have an introduction, many people in the startup world are approachable with a cold email.

Guy Kawasaki, former chief evangelist for Apple, and author of 13 books including The Art of the Start 2.0, wrote a fantastic post, “The Effective Emailer,” on how to craft that all-important message with your ask.

Another great take on the email ask is from venture capitalist Brad Feld, “If You Want a Response, Ask Specific Questions.” This post offers advice on how not to approach someone. The title of the post says it all, if you want a response, ask a specific question.

Ask for the Sale
Many startup founders don’t have sales experience and so often miss this incredibly simple, yet incredibly important part of sales: asking for the sale. Even in mass-market B2C businesses, you’ll be surprised how easy and effective it is to ask people to sign up. Your first sales will be high-touch and likely require a big time investment from your team. But all of that work will go to waste if you don’t say, “Will you sign up to be our customer?” And if the answer is a no, then ask, “What are the next steps for working with you?”

Empower Yourself
It’s empowering to ask for something that you want. This is the heart of my grandmother’s advice. She is and has always been an empowered woman. I believe a big part of that came from not being afraid to ask for what she wanted. As long as you’re polite and respectful in your approach, step up and ask.

The opposite of this is to meekly watch the world go by. If you do not ask, it will sweep you away on other people’s directions. This is the path to failure as an entrepreneur.

The way to empower yourself in this world starts with asking for what you want. Whether it’s something as simple as asking for a special order at a restaurant or as big as asking for an investment, make that ask. After all, you’ll never know unless you ask.