The Two Things I Do Every Day as a Leader. What Are Yours?

I am perfectly imperfect in my execution, but I always strive to live up to my best self on my best day all in service of my team.

Someone I deeply respect once told me: “You can manage someone or something into the ground, but you can only be considered a leader when you inspire.” This idol of sorts went on to say: “And to inspire, you have to be accountable, consistent, and admit when you come up short.” I leaned in further to hear (my idol was aging fast, but I remember it like it was today): “And above all… you must give up more power than you wield.”

The data points I use as a leader: did my values and intentions on the (Left) translate into unlocking and unleashing people to the point that they wrote me a letter (Right), email, text, or LinkedIn rec letting me know that I lived up to my values and intentions? It’s just that simple.

And so, while the we all navigate what safety and security looks like for ourselves, our families, communities, and our economies… ask yourself in this moment: how will you lead?

Will you fall back on conventions that were taught to you or standards that you were measured against because you had to fight hard, pulling yourself up by your bootstraps, running the traps of misogyny and racism—or will you interrogate systems, market rates, titles, roles, and requirements that are most likely wrought with systemic biases?

To kick things off, I will start with my own two commitments:

TL;DR: I serve my team and I help deliver excellence at scale.

What do these two things mean in practical, lived reality terms?

Here’s more than you’ll ever want to know about my leadership—not management—philosophy…

Commitment №1: Servant Leadership

• I lead at the pleasure and privilege of the teams I serve on.
• The team is always my first priority in all I do.
• I lean in when the team needs me, and lean out when the team has it under control.
• I cede power and position in the interest of growing big people to do giant things.
• I operationalize and weaponize my team’s individual and collective greatness by unlocking, unleashing, and sponsoring them to do their best and greatest work.
• I lead small teams to do big things, not because I went to school for a Masters of Business Administration, but rather because I combine hard earned experience with exceptional and intentional role models, teachers, mentors, coaches… and improving on the unfortunate consequences of bad managers above me / around me.
• I believe this qualifies me to have a MRWB (Masters of Real World Businesses). I also specifically hire for other MRWB graduates and look for talent that is coming from overlooked and under-appreciated places (see especially my piece: “When it Comes to Talent, You Stay Be Doing it Wrong”).
• Hard earned experience means I have losses, wins, and learnings that can only come from being wholly responsible for revenue, team health, strategy, and execution for not one, but two game-defining agencies: J3 and Made by Many U.S. I have also had failures along the way that propelled me to learn more and dig deeper into fields that have been emerging in the hollowed out shells of Advertising and Marketing (hint: it’s Product and Technology… for good, with kind human intelligence, with good humans at the core).
• These learnings are also something I give freely and regularly as a consistent contributor to those around me on the come up as a part of TRTL Ventures and Turtle Academy. My turtles are stronger, wiser, healthier, and more themselves due to my commitment to something bigger than myself.
• I also have built my philosophy from the embers of the sparks I helped create: when people are seen, truly seen, and heard, and listened to… you can find stupendous applications for their giftings, and they can show you how to unlock ideas further and better, too.

Commitment №2: Help Deliver Greatness at Scale

• I live my talk in my walk. Consistently, quietly (and sometimes loudly, if need be), and for those under-represented in the upper crust of today’s corporate ranks. From mentoring and developing over 500 “turtles” in Turtle Academy over the last 15 years, you will know me first by my acts and second by the acts of those I have unlocked and unleashed.
• I am a life-long ally and activist for those who do not look like me, but need to be seen to be heard to be their full selves so the world becomes more like the place we all want to inhabit: equitable, safe, healthy, and filled with joy. Since my mother first explained—and walked her walk in explaining—to me and my sister about what happened during the Civil Rights Era as her church was one of the only de-segregated-from-the-jump havens who walked their talk of inclusion, love, faith, hope, and charity… to when I realized we didn’t have a lot but there were kids at school who had even less… to when I spoke up and out for Gay Rights in 7th grade when the Oregon Citizens Alliance was trying to pass a hateful piece of legislation…. to when I testified with Planned Parenthood at the Oregon State Capital for safe access to legal abortions in high school… to when I brought the ACLU into my high school when they banned tank tops because boys were snapping our straps and the School Administration needed to be shown that it was a behavior-correction issue (YES: boys need consequences) and not a civil-liberties-editing issue (NO: girls need to dress modestly so as not to invite assault)… to taking courses in race, gender, sexuality that led me to write a thesis that critically examined the heteronormative biases in my high school sex ed curriculum (that I attribute to the life lost of one of my dearest friends, who did not see a life arc for him in the narrative that Junction City projected back in the late 90s early aughts)… to launching an Academy and Venture Fund for students aka Turtles who were in need of a bright light, financial support, and a platform to understand, navigate, and negotiate with power structures built by mostly straight, mostly white, mostly male overlordTs… to launching Purposeful Privilege… And so on and so on, ad infinitum. Until my last dying breath.

I stand for with all who are ready to take the hard, imperfect, bridge-building, bias-burning next steps in enacting meaningful change for BIPOC, LGBTQIA+, immigrant, rural poor, female-identifying, and at-need communities who have long been underserved, under-networked, and over-emotionally-taxed by a world that wasn’t built for them.

• I am qualified because I have been training for this my whole life — from humble beginnings that looked fancier than they were in Northern California and Rural Oregon… to sport courts and lumpy bumpy Oregon fields that taught me teamwork… to State Houses for mock trials and debates to real testimony to back my beliefs… to boardrooms and multi-million dollar pitches that led me and my teams to build and scale-up JESS3 (2006–2012) and Made by Many’s U.S. presence (2014–2016)…to being hands on and boots-on-the-ground to drive forward early days net-new innovations at Intel (Social Media Center of Excellence and Intel iQ 2007–2012), Nike (NIKEiD and Nike DTC social media 2010–2016), P&G (various BU-led innovations 2017–2019), and TD Ameritrade (Team Nimbly 2019-present).

I lead by getting my hands dirty, my heart involved, and my eyes on the horizon to clear the bush, bureaucracy, and naysayers so the team may do their best work.

These two commitments are at the tip of my fingers in light of:

• Taking stock of how I lead in my full time role as Entrepreneur in Residence at Bionic as I work with the incredibly talented and kind team at Nimbly, as well as our other determined agents-for-change at our Partners who are pre-launch with us.
• Taking stock of how I lead in the Partner role I play at Bradshaw Vineyards where we are working through how to make Harvest safe and equitable for all — which it always has been and will continue to be how we build our team, especially when we have Covid safety precautions to design for and a dangerously racist administration to shield our Latinx team members from.
• Taking stock of how I lead in the co-founder, CEO, and Venture Partner Role I play at TRTL Ventures Turtle Academy where we have an active portfolio of 10 companies, are raising another round to support others, and have over 500 Alumni/Alumna/Alumnum + current students.
• Taking stock of how I lead in the co-founder and CEO role I play at Purposeful Privilege where we are helping provide practical and tactical ways to courageously continue the initial activism millions of us took part in for Black Lives Matter.
• What I wanted to do with my time and privilege on this earth, which Covid has uniquely and harshly given me space to reflect on (see my previous post “What does having 20/20 Vision in 2020 mean for you?” for some of the exercises I used to arrive here).

Here’s to you, young leader stepping up and into your greatness. You’ve got this.

Keep your head up and heart open. Keep your cup filled, do lots of self care, and know where and how to throttle your speed (and your breaks).

Continue to turn the excuses and chips on your shoulder into adaptations and opportunities. Never stop caring. Find your tribe.

And if you need some more blessings and mantras, I got you! I have a six-part blessing awaits you here and a survival guide awaits you here (and if you can’t get enough of my mixed metaphor, all heart advice… I also gave the Commencement Speech at my high school in 2016 because as imperfect as my town and experience was there… it was also a place that showed what unconditional hard work could do in the fields and on the field).

And to the Ancient Millennial leaders (like me), GenX leaders, and salt and pepper leaders who are creating space and opportunity for those who are on the come up: thank you.

Thank you for giving these next gen leaders a chance to be hands on in the roles you currently occupy.

Thank you for sponsoring them when you have colleagues say “I’d love to give this person the opportunity, buuuuuut…. [insert excuse about ‘not quite ready’ and ‘hasn’t yet done X’]”

I see you pushing back on these well-meaning colleagues to point out that they can’t learn how to lead without first getting a chance to lead. And you are the first in the line of line managers to be a real, true servant leader.

You know that no amount of articles, workshops, conferences, books, or empty promises for development will ever replace the one true teacher: Experience

Here’s to all those in the field earning their Masters in Real World Business.

Here’s to all those elder statesmen and women who are stepping out of their roles as managers and into their callings as servant leaders to deliver greatness at scalte.

I salute you.