Thank You Mr. Venture Capital

I missed him at the start. Father Time had taken its toll, which blurred my initial recognition. The old white man wand had cast its usual spell as none of his aging features were unique. Silver swept the top of his head outlined by a hairline that emulated low tide, retreating to the back of his dome. His once stiff posture was now concave, akin to an aging cyclist. Adorned in a blue, Brooks Brothers button-down and dark jeans, he was dressed the same, sans a black fleece vest, a popular accessory amongst his people. 

As I rose for Intermission during a Sunday night performance of Funny Girl, I locked him in and all the feels came racing back. Almost 10 years ago, Mr. Venture Capital (VC) blocked me from landing my dream job. Silently, I celebrated that I was closer to the stage than he. But, I also must credit the man who attends this Barbara Streisand-inspired showcase. He didn’t see me, and even if he did, no glint of recognition would appear. Former female tech execs in their 50s are not on his radar of interest. 

Flashback to 2016: I was amid a love affair with one of his CEOs. Internet horn dogs will be sorely disappointed to learn that it was strictly professional and platonic. Physically,  we were polar opposites. I was the less attractive version of Brigitte Nielsen in Rocky IV, and his presence was akin to that of Alan, Michael Cera’s character in Barbie. Our emotional connection was instantaneous and further cemented with every round of interviews. When I entered the room, his face would light up as if I had just gifted him Taylor Swift tickets. Both of us suffered from diarrhea of the mouth in the presence of the other, obsessed with inspiring and motivating employees in a start-up environment.  When the laughter began, it was difficult to stop as we struggled to refocus our attention on the future of the business. 

It was difficult to stop until it came to a screeching halt. 

“I’m so sorry Kerri but we can’t continue the interview process.” Anticipating a job offer, I was blown by the brutal contradiction. Sinking onto the sofa behind me with my rapid breath-stealing speech. “Wha-wha-what do you mean? Why? What happened?” Betraying his source, he revealed that Mr. VC didn’t believe that I possessed the right skill set for the role. “Quite the assumption, considering that he never interviewed me.” He didn’t have to. According to “Alan,” sixteen years at one company failed to demonstrate the “entrepreneurial spirit” necessary for success at a small start-up. Like the salesperson I was, I replayed my strengths to perpetuate the FOMO feeling of failing to hire me. I was speaking to the choir. Squeezing out a “thank you for your time,” I lay down and wailed.  

Devastated then, but thankful now. What I believed to be the best outcome at the time was not. Not even close. 

As our daughter closes out her junior year at Northeastern, the stress of searching for a job post-grad is beginning to take hold. The “what ifs” claim her brain like it’s their personal playground. Anxiety gives her a sense of control vs. letting life flow. Apple doesn’t fall far. Exhausting all clichés, I relay the story of how a journalism major with dreams of doing PR in the Windy City thankfully fell into sales in the Rockies. 

It was 1994 and job prospects for most college grads were meek. The factors fueling this difficult hiring climate no longer reside in my memory bank. Having just completed a six-month internship at the United States Professional Tennis Registry in Hilton Head, South Carolina, I thought I was the GOAT. Game to go anywhere at any time, throwing my CV all over the planet trying to target sports marketing roles. Naive me had no clue as to how competitive gaining entry into this industry was and continues to be. No network connections, no bueno. 

Rejection after rejection forced me back to my parents’ place in Blacklick, Ohio (horrifying name, I know), which was not my childhood home. Far from it. Watching Diagnosis: Murder, starring Dick Van Dyke, on a Friday night with both your parents in the ‘burbs as they melt into their matching La-Z-Boy recliners is depressing with a capital D. The big bangs were now gone and neon was no longer a wardrobe staple but, the line of questioning faced while attempting to escape was reminiscent of my teenage years. “Where are you going? Why? With who? Who’s driving? Do I know them? When will you be home?” The GOAT was now the joke. 

A lifeline was finally thrown, yanking me from the crime dramas and other creature comforts curated for baby boomers. I would miss the subsidies. My best friend from college had successfully landed a PR job in Denver and before the invite left her lips, I was driving cross country in my beige Toyota Corolla with a basketball-size dent on the side, courtesy of yours truly. Despite their signal stating otherwise, never assume someone is turning right as you look to cross their committed path to make a left. Like the Cybertruck, she wasn’t pretty, but she reliably drove me to Denver, with the accelerator intact. 

Adding a new sleeper sofa to my friend’s one-bedroom apartment at 6th & Pearl, I became a permanent fixture in her living room between interviews. Upon her return home, a large sigh assisted by an eye roll would be seen, heard, and felt if the sofa was still in sleeper mode. Translation being: “Get a life.” Who knew that temping at a commercial printing firm in the warehouse district of Denver would provide the first signs of “life.” I was offered a full-time position as a sales trainee, making $20k/year + commission. Not PR. Not marketing. Not sports-related. I was selling pretty paper. 

Sales stuck. It followed my career to Boston and continued onto California. In my last role before retirement, I had a full circle moment, returning to my PR roots. I hated it. Due to the departure of our VP of Comms and a lengthy executive search, I filled the role for almost a year. Selling a high-tech narrative to an audience of reporters, who are incented by impressions and clicks, is like serving a perfectly grilled Japanese Wagyu to a dinner guest, who douses it in ketchup before their first bite. Days would be spent educating the media, only to see the resulting headline buried and woefully inaccurate. 

Sales was storytelling. Reading the room, absorbing every detail, identifying the one individual dragged to the table beyond their consent. Pitching to their forehead as the laptop screen swallows the rest of their head, nodding in agreement without listening. One eyebrow rises, a tiny sign of intrigue, you grab it and expand upon their topic of interest fervently. Slow down. Take a breath. Confirm all are following, “does that make sense?” The “forehead” closes their laptop, sits back, and smirks, acknowledging your exhaustive efforts. That’s all the fuel you need to keep going. You keep going and going until you hear those token words, “Let’s take a look at the contract.” Goooonnnneeeee! 

I loved sales and therefore, excelled. Or, I excelled and therefore, loved it. Both can be true. Sales was never seen as the “best outcome” when I was 22 or even 32, for that matter. Yet, it was. 

Peyton, baby girl, your intended path may not always be the best path. Be open. Be curious. Be you. “Why life is unfolding the way it is and what may be coming next is so far beyond your pay grade to know. Might as well surrender to the flow.” @corymuscara/Insta. 

I could have requested an interview with Mr. VC, an opportunity to make my case. I didn’t. Instead, I chose to let fate determine my next place of employment, which turned out to be Honey, the browser extension company. In 2018, PayPal acquired Honey for $4 billion. Mr. VC’s portfolio company was also acquired for $17.5 million. Almost the same. Not. I later learned that he had passed on the opportunity to invest in Honey. Thank you, Mr. VC, for blocking me. 

My Drug of Choice

Like a string of cooked spaghetti draped on a fork, I was caught on a poor sapling with skis still glued to my boots. If I was at yoga, my posture would have been an impressive one. On the side of a mountain with no leverage or assistance in sight, it was painful. I had followed my husband into a tunnel of trees, who breezed through the aspens and pines as if they were invisible, vanishing from view.

I was all alone. 

Repeatedly, I tried to launch my body upright, only to topple back onto my new found friend, taking tree hugging to the nth degree. It failed to provide me the necessary leverage but I was thankful for its diminutive size, saving me from Sonny Bono’s fate. With a loud roar to fire up my core, I performed the largest side crunch of my life and extracted myself from its grasp. My obliques breathed a big sigh of relief. The tree, not so lucky. Any hope it had of capturing the love and attention of a Charlie Brown was banished by my body weight. No Christmas specials for you my friend. Apologies.  

I was exhausted, disheveled and defeated but thankful to have all limbs intact. No ski patrol with sleds in tow required. Like a snail, I cautiously made my way down the mountain to the chairlift responsible for transporting me to the site of entanglement. My confidence killed in the trees. I emerged to find my husband, looking like a North Face ambassador, waiting with concern. “What happened!?” The fresh scratch on my face spoke volumes but I responded, “I followed you.” 

While sky high on the chairlift, I pondered, “why am I constantly putting myself in situations where I don’t feel good enough?” My goal for the 2024 ski season was to become more proficient at skiing trees. Why? Do other 51-year old women establish similar goals, especially ones that broke seven bones during the previous ski season? Why can’t I find joy at my current level vs. pushing myself to the next one, fueling the “less than” sentiment? Is it healthy or harmful trying to be exceptional at all that you do? 

When I posed this question to my therapist, she surmised that this behavior was most likely tied to my relentless pursuit for approval. I should have known. Even in my retired state, the approval junkie strikes again. Fug. 

Growing up in Green Bay, it was all boys on our block. Skateboarding and BMX bikes dominated the streets in the Summer and snowboarding would take over as the first flake fell on the mole hills of upper Michigan. “Ski Brule - the best mountain in the Midwest!” Camped out on the curb with our locks feathered like Farah Fawcett, my best friend Maureen and I spent hours watching, whistling and waiting for male attention. There may have been a crush or two, but I was fixated on their athletic prowess and no fear attitude as they skillfully executed trick after trick. 

In search of the boys’ acceptance and approval, Maureen and I were challenged to rise from the curb and discover our own demonstrable skills. Our toolbox of skateboard tricks failed to extend beyond the nose pickup. But, give us a board, jump rope and a ten speed, we were Michael J. Fox on the hoverboard in Back to the Future. Flying over potholes and pavement cracks while screaming “faster, faster” to the designated driver was a daily ritual during the Summer of 1985. It took weeks of honing our craft but we finally heard those golden words of validation from the gaggle of guys, “holy shit you’re going fast!” Maureen and I looked at each other, smiled and yelled, “hell yeah!” 

We were in…assuming we survived the duration of the Summer. ;) 

Flash forward to meeting my husband. Raised in Southern Vermont on skis, dirt bikes and race cars, Daryl is also an exceptional athlete. Surprise, surprise, I married one of the boys from the block. At the onset of our courtship 25 years ago, I have vivid memories of parading my alpine skis through the living room. “Look at me and my skis!” This attempt at flirtation failed to register as a critical attraction factor as Daryl has no recollection of this performance. Watching him expertly maneuver a snowmobile on the Canadian trails or launch his jetski on the ocean-like waves of Lake Winnipesaukee were definitely factors for me. My father-in-law once asked, “is it your life mission to beat Daryl at just one sport?” Not exactly. Securing his athletic approval trumped beating him at a specific sport as it served as a source of self-esteem.  

My approval pattern followed me like a golden retriever as I embarked on my career, IQ replacing that of athletic prowess. Superior intellect along with an Ivy League degree were the targets of my mission. If an individual possessing this pedigree chose to employ me, collaborate with me or invite me to lunch, I must be smart too! This inclusion quieted any conflicting thoughts or memories of Mrs. Roy berating me in the presence of my fourth grade peers for failing to construct a pentagon on my goddamn geoboard. When my prey was a superior or individual of influence, I justified my approval-seeking actions as a necessary evil to guarantee the success of my responsible team. More often than not, I was right. Budget approvals, salary bumps and promotional opportunities are synonymous with having your manager in your hand. While at Commission Junction, I earned four promotions over the course of eight years, becoming the youngest President of a division at 35 years of age. 

The pursuit of approval can also punch you in the gut. Still working in Boston, I had inherited a new boss and his first order of business was to collect the executive team’s feedback re: the state of the business AND one another. To be handwritten, we were assured all responses would be kept anonymous. You see where this is going? Shame on me for failing to question the handwritten component as I dutifully responded with my brutal feedback. “Aye, aye Captain - let’s get this ship back on course!” As the only team member on the East Coast, I was forced to scan and send my pages to Cali. The following week, he reviewed the pages - adorned with my very distinct handwriting - with each of my West Coast peers, face-to-face. One of these peers was my former manager, mentor and friend. Oomph. I too received several harsh comments but being over 1,000 miles away, I had no insight into the source as the pages were hidden from view.

Despite dozens of apologies, I deservedly lost a friend. A true friend would have delivered the feedback directly, not via the lips of a drooling demon. My approval-seeking self feared that such feedback would implode our friendship. Instead, I sought the approval of another by selling my soul to the devil. It was a vicious cycle. 

It was not by choice to work for the Captain. He had replaced our previous manager and none of us had the privilege of interviewing him prior to assuming the helm. Interview or no interview, his actions quickly proved to contradict our previously-held value system. Some left. Some fired. Some stayed and played the game. Operating in the last camp, yours truly was ultimately chosen as his successor following his own promotion. Hate the game, not the player. I’m such an asshole. 

To be successful, one of the unwritten rules of the game is that you will NEED the approval and support of your superiors. Shocker, I know. Value alignment is key to keeping your integrity intact. When your values are aligned with the company and culture, seeking the approval of others will be in support of your authentic self today and the person you want to become tomorrow. Are you asking the right questions during the interview process to help ensure such alignment? Have you spoken to former employees to get the good, the bad and the ugly? I can count on one hand how many calls I’ve received re: previous employers.  

Below are some sample questions:  

• What is the feedback culture at Company X? Is there a formal review process? If so, what is the frequency? Does it include 360-degree reviews? Does the CEO participate? Does the company engage in forced ranking? Do salary adjustments occur together or separate from the review process? On the daily, how is constructive feedback delivered? Can you give me an instance when an employee disagreed with a member of the executive team? How was that information received and addressed? 

• When was the last time that Company X was forced to do a layoff? In the spirit of privacy, what were the termination factors and how was the news delivered? What was the severance package?

• What is the role of human resources at Company X? Are they driving business decisions or merely supporting them? Do they have a seat at the executive table? Are they a key stakeholder in organizational design?

• If you HAD to change one thing about the CEO (and your manager-to-be), what would it be? 

• What is the process for making critical decisions? Such decisions could include sunsetting products or projects, new strategic initiatives, budget approvals, etc. Who is involved in such decisions? How are they communicated to the rest of the organization? 

• How does the management team communicate more broadly? What is the cadence of communication and how is it delivered? Are they open to Q&A sessions? How often does the executive team “walk the halls” or visit remote offices? 

• Tell me about a time when Company X was under significant pressure (i.e., earning targets missed, etc.). What changed to get the organization back on track? New goals? New hires? New attitudes? 

I encourage others to provide additional questions via the comments section of this platform.

I skied by myself several times this season. No trees. No fear. Just fun. Admittedly, I got bored after a bit and was chomping for a challenge, but refrained in lieu of safety. I’m happy to report that my skills have significantly improved amongst the trees and no more saplings have been harmed. But, when my husband and I are about to embark on new, difficult terrain, I stop and ask myself the question, am I doing this for me?

Why I Went Back to Therapy

The three of us climbed back into my clown car (aka BMW i3) with our CEO assuming shotgun. Big and soft, he possessed the build of a retired football player, giving him default access to the front seat, regardless of title. My direct report was the polar opposite in stature, squeezing her small frame through the suicide doors and landing her bum with a successful “ha” in the barely-there backseat. The gymnastics required to enter and exit this vehicle never ceased to be a source of amusement. 

“I think they’re going to sign,” stated our CEO as we sped towards the 405 and away from the prospect’s office on Sunset Boulevard.  

“Why so confident,” I inquired. “We have no knowledge of their budget cycle or if any of the meeting participants was an actual decision maker.” 

“Why didn’t you ask!?” He barked. 

Months of frustration raced through my body. Feeling like a volcano, a hot lava was coursing through my veins, desperately seeking an outlet. Attempting to keep the angry flow inside, I assumed a death grip on the wheel. My grip quickly slipped and I shouted, “how!? How am I supposed to ask any questions when you won’t stop talking!?” Eyes wide and mouths open, both passengers were in shock as I screamed inside this small container of a car. “Every meeting you pummel prospects with our pitch, vomiting on everyone until there is nothing left. No time for questions. No energy for feedback. No discussion of next steps. Nothing.”

Like Harvey Specter from Suits (I wish!), he defended his sales methodology as if Judge Judy was our fourth passenger so our debate persisted for the duration of the drive. My words were overdue. But, I regret my tone, approach and creating such a scene in the presence of one of our colleagues. Not cool. 

How the hell did I get here? Repressing my emotions - repeatedly - proved to be the perfect recipe for such an outburst. Professionally and personally, I had been living by the philosophy of, if it’s not going to change anything, don’t say anything. Our CEO wasn’t going to change. I needed to learn how to adapt or leave. I chose the latter. 

I recently returned to therapy as my repression pattern was decimating a personal relationship that I didn’t want to leave but was struggling to manage.

“How did she respond to your feelings,” my therapist asked. 

“Oh no. These thoughts never left the inside of my head,” I responded, looking away from her face and fixating on the piece of lint perched on my knee. 

Too many to count, the number of conversations with me, myself and I. If it’s not going to change anything, don’t say anything. Challenge was, it was changing me and not for the better. 

When did I stop sharing my feelings and why!? Childhood trauma? Years of working for men that repressed their own emotions in fear of appearing weak and therefore, unable to deal with the vulnerabilities of others? Did I fear that such feelings would create friction, leading to my eventual termination from a job or relationship? 

Yes, yes and yes. Fear of abandonment strikes again. 

According to a September 2016 issue of Harvard Business Review, “Leaders expect to influence how people think and behave on the job, but they may feel ill equipped to understand and actively manage how employees feel and express their emotions at work. Or they may regard doing so as irrelevant, not part of their job, or unprofessional.” The article goes on to state, “by not only allowing emotions into the workplace, but also understanding and consciously shaping them, leaders can better motivate their employees.” I recognize this is the anti-Elon Musk school of management. Another topic for another day. 

I’ve been on the other side of the equation as a manager attempting to “shape” the emotions of my responsible team members. Courtesy of nature and nurture, Brenna wore her emotions on her sleeve. Not a fan of our recently-hired head of marketing, she informed me of this sentiment during every exchange. There were tears as she feared a pending culture change from one of caring to coldness. Brenna’s creative spirit was dying a slow death, injured by the robotic nature of our new employee. 

With several critical campaigns on deck, I needed them to successfully collaborate so I put on my coach’s cap and crossed my fingers. Once I understood the underlying issues, I encouraged Brenna to address Eve, our head of marketing, one-on-one and assisted her with the talking points. I also spoke to Eve directly so she knew that I was aware of the conflict along with my proposed resolution. They never became friends but a communication channel was created so they could professionally - and respectfully - work through any challenges faced. It was never easy but we made it work. 

If Brenna hadn’t been comfortable in expressing her feelings, I may have lost a rock star performer during an important period for the company. About a year later, she did indeed leave the company but was running to something vs. from. Note to self, Brenna’s feelings never created friction between us. Terminating her employment was never on the table. Even if it was, Brenna had the confidence and knowledge that she would be just fine without us.  

I could learn a thing or two from Brenna. 

A moving vehicle seems to be my desired destination for contentious conversations. Mountain living has replaced my BMW i3 with a big, blue Bronco. Equipped with 37” tires, gymnastics remain a driving prerequisite as a springboard for entry would be appreciated by all. We were heading back to my abode following a fruitful day of shopping. I possessed no expectation of change. Blame was not my intent. My goal was to let go and move forward. The only way for me to do so was to invite another to my one-sided conversation. As my therapist reiterated, this was to be the first of many as we repaired our relationship. 

No volcanos. No outbursts. I shared my feelings slowly and kindly. With every word, I could feel the weight on my chest retract, pound by pound. She didn’t pull a Lady Bird, launching herself from the vehicle and right into a cast adorned with, “fuck you Kerri.” She was defensive at times, trying to turn the table. Thoughtful too, reflecting on her own childhood in an attempt to understand past behavior. Most importantly  - and like Brenna and Eve - a communication channel was opened in order to tackle difficult conversations in the future. 

“If it doesn’t change anything, don’t say anything” is a terrible philosophy. “Grin and bear it” is bullshit. Silence is not just deafening, it’s dangerous to yourself and others. In the words of author Bessel van der Kolk, the body keeps the score. Bottling your emotions may manifest as physical pain, anger, insomnia, overeating, drinking/drugs, media binging and/or depression. Ambien was a very good friend when I worked for the CEO referenced at the top of this post. I’m pleased to say that we are now enemies. :) 

For your own health and wellbeing, free your feelings. You never know, your words could change someone or something, including you.

Is “Pressure a Privilege” or a Prison?

His mouth was pressed to her ear as they walked together in rapid fashion. She stared straight ahead, shoulders high, uncomfortable with the hotness of his breath. Despite her discomfort, his mouth remained until he was forced to retract. “Batter up!” Not a couple strolling down the street but my daughter and her softball coach en route to the batter’s box. Barking instructions, he resisted the urge to rip the bat from her hands so he could serve as the designated hitter. “Keep your elbows down. Bat high. Level up.” 

If Peyton failed to make contact with the ball, he would resume this position - and a sharper tone - as she crawled back to the dugout. 

Watching this man staple his mouth to my daughter’s ear, I wanted to scream. Just like her Mother, Peyton is her harshest critic. It was as if I had crawled inside her, the pressure pounding on every muscle, tightening with every breath. I looked down at my lap to disguise my watering eyes. My clenched fists barricaded beneath my thighs to prevent injury to myself or others. 

You are going to crush her. Back off. Let her be. Please!

On the field or in the office, who does their best work when under the thumb of another? I don’t. I used to work for a CEO that called me - multiple times - every weekend. I never knew when or why so I failed to fully decompress while spending time with my family. Was a client threatening termination? Did an investor threaten him? Was payroll in jeopardy? Nope. None of these things. Typically, he was playing big brother, watching the poor use of his platform by one of our clients and demanding that we re-educate him/her/they immediately. 

I was not the lone recipient of our CEO’s frantic outreach. It was a Monday morning ritual with my colleagues to share our crazy call stories. Marcy was the envy of us all as she was a pro at picking up the phone and immediately putting the call behind her in order to enjoy the duration of her day. Why did it take me hours to do the same? 

According to Nick Petrie, co-author of the book Work Without Stress, “pressure is not stress. But, the former is converted to the latter when you add one ingredient: rumination, the tendency to keep rethinking past or future events, while attaching negative emotion to those thoughts.” 

Rumination. Meet the Queen. I was thinking about those damn weekend phone calls before, during AND after. Was it my attempt at control? I detest surprises so if I can map out every potential scenario, I’ll be mentally prepared for any challenge faced. Despite my best efforts, our CEO successfully surprised me 90% of the time. Every phone call was followed by cursing and me contemplating the situation for hours thereafter. 

It makes me sick to think of the number of days stolen by rumination. The number of conversations that never left the inside of my head. Time lost with my daughter. My husband. My friends. 

Thankfully, Nick has tricks - in which I’ve added my own two cents - to prevent us from falling down the rabbit hole of rumination. 

Wake Up: While President of Commission Junction, I commuted 60 miles each way from my home in Thousand Oaks, CA to our offices in beautiful Santa Barbara. This journey included one of the most beautiful stretches of Highway 101 as the ocean tried to get my attention for 30 miles of the drive. Most days, I had no recollection of the commute nor my surroundings, rumination ruling my brain.

Snap out of it. Focus on the present. Return to your youth by seeking out a selected color on long drives and walks. Play the license plate game. As Nick says, “reconnect with the world,” which may require physical movement such as clapping your hands, moving your body, etc. What do you hear, smell, see and taste? 

I had the privilege of working for former Major League Baseball player, Shawn Green, at a start-up that he co-founded called Greenfly.  When on deck, he would slam his bat against his cleats to exit his head and lean into the physical. Being present is critical when you are the primary focus of 40,000+ fans! 

Control Your Attention: I had no control as to when our CEO would call me. But, I could control my reaction. I could establish boundaries and block his call to return it when it was most convenient for me. Admittedly, I feared such a boundary would reflect poorly on my work ethic along with my willingness to “do whatever it takes.” Or, instead of story swapping with my colleagues, I could brainstorm with our CEO to identify a better approach to managing these moments of anxiety for both of us. 

If your mind enters obsessive mode, Nick suggests “drawing a circle on a page and writing down all of the things you can control - or influence - inside of it. All of the things you cannot outside of it. Remind yourself that you can care about externalities — your work, your team, your family — without worrying about them.”

Put Things in Perspective: I’m watching the U.S. Open as I write this in which Billie Jean King is being honored for successfully fighting for equal pay in tennis 50 years ago. One of her infamous quotes is showcased every match, including my favorite of “pressure is a privilege.” Coco Gauff expanded upon this awesome phrase in a recent press conference stating, “too many families have no idea when they’ll see their next meal. The fact that I get to play a sport I love...is a privilege.” 

Yes it is. 

Nick also recommends that you pose the following question, “how much will this moment in time matter in three years?” In short, take a breath, a step back and break out of your bubble. A former colleague used to yell through the halls of affiliate marketing company Be Free, “we’re not saving lives, people!” I wish our digital marketing platform rescued those challenged by death but it did not. 

Let Go: This one is the hardest. How does one find peace when faced with a difficult situation or individual? Our CEO was not going to change so I needed to accept him as is or leave. To stop the hamster wheel of thought, Nick also recommends asking yourself, “what have I learned from this experience” and “is there an action to be taken?” One client in particular was a repeat, weekend offender. I suggested to the customer success rep that we contact the client before the weekend to understand their intended use of the platform and provide a brief tutorial, if necessary. The CEO calls didn’t stop but they were cut in half. 

Yoga, meditation, journaling and therapy are also excellent tools in learning to let go. I do them all! 

Peyton faced a full count, three balls and two strikes. Unless she fouled out, the next pitch would be the decider. I couldn’t watch. I heard the bat meet the ball with a crack. My head snapped back to find its place in flight. The shortstop jumped, stretching her body to its maximum potential. The ball soared just beyond her glove. She rounded first base and raced on, bringing her teammate home. Like a traffic guard, the third base coach stopped Peyton in her tracks at second. Her shoulders dropped, we locked eyes and she broke out in a big smile. 

On the drive home, I asked her, “how did you do it? Perform under his thumb?” She sighed in response. “Mom, the coach has control issues, which have nothing to do with me. I just do what I can do.” From that point forward, I stopped projecting and started loving my girl at the plate, strikes et al. 

Congratulations to Coco Gauff on her first major title win!

The Cult of Charisma

I had heard the same story at least 25 times in the last 12 months. He shared it with the same cadence, charisma and hand gestures. It was magic every time. His magnetic, messiah energy loomed large, encouraging all to hang onto every word. How the business came to be and the vision that would change the world. Childhood trauma prompted him to quickly assess the room, identify any threats and diffuse them with a smile. The story recipients laughed at the same moments. Nodded their heads simultaneously. Drinking it all in. Tears filled the eyes of some as he shared his early life of poverty, leading him to this juncture. Consciously or subconsciously, they were falling in love with the man, the idea and the potential.

I fell in love too. Before the epiphany hit me, charisma alone can’t scale a business. The impact of the founding narrative has a shelf life. Unfortunately, employees of WeWork also learned these painful lessons with unfathomable outcomes: job loss, worthless equity and so much more. 

At the onset of my retirement in early 2022, I fell down the WeWork rabbit hole, reading several books about the dysfunctional company such as the Billion Dollar Loser and the Cult of We. Obsessed with Jared Leto since the 90’s cult classic My So Called Life, I also watched the Hulu docuseries WeCrashed and listened to the supporting podcast with Professor Scott Galloway.  

I was fascinated by the fact that this man with little to no business experience raised $22.2 billion dollars in venture capital resulting in a $47 billion dollar valuation. Yes, $47 BILLION DOLLARS. A unicorn on steroids. Despite claims of being a “serial entrepreneur,” his only attempt prior to WeWork was a failed clothing company called Krawlers, which made knee pads for babies. Slogan being, “just because they don’t tell you, doesn’t mean they don’t hurt.” 

Adam, they really don’t hurt. ;) 

With a height of 6’5” and shoulder-length, wavy hair, Adam’s unique presence dominates every room he swaggers into. When former employees and investors describe Adam, the number one attribute used is “charismatic.” Childhood stories of living on a kibbutz in Israel combined with moving to 13 different homes in 22 years fueled his compelling - and repetitive - narrative of community. “The power of we: be part of something that is greater than yourself.”

Who knew the business of leasing offices and dividing the space into shared desks could be so compelling? 

Sadly, Adam Neumann is not the only one. Venture capitalists seem to be suckers for charismatic and courageous founders - especially men -  with little to no business experience, i.e., Sam Bankman-Fried and Travis Kalanick. I know, I know Elizabeth Holmes of Theranos should also be in the Adam camp. Done. I also know most - if not all boards - pressure founders to hire experienced executives to offset their ignorance. But, how do they ensure that these founders actually listen to their savvy C-suite? Adam didn’t. 

(Looking at gender alone, all-women executive teams secured a mere 1.9% of the $238.3 billion in venture capital allocated in 2022. This percentage increased to 17.2% when the team was of mixed gender (TechCrunch, January 2023). 

I was a sucker too. I worked at three, different start-ups during the course of my career in which several of the male CEOs had no operational, business experience and struggled in listening to those outside their circle of trust. This circle typically included family members, early employees or college buddies. People like people like themselves. 

A victim of my own Ivy League envy and perceived emotional intelligence, I jumped onto their executive teams and followed blindly. I quickly found myself managing their ego instead of doing what was best for the business. When the six-month honeymoon period came to a close, I started to dismiss my 20+ years of experience and assumed the tactics outlined in the latest book read by the CEO. Reid Hoffman’s Blitzscale still gives me nightmares. 

At one such start-up, I was tasked with accelerating customer acquisition. The company’s growth was starting to slow so I was hired to craft a new global strategy and hire the necessary resources to execute. After weeks of researching the market; assessing the competitive landscape; interviewing employees; understanding our customer base along with the key attributes of top clients, I presented a robust strategy including the necessary marketing infrastructure for success. It gained the unanimous support of the executive team and board. At first...

Challenge was, targeting small to mid-market businesses isn’t sexy. Despite the lack of product-market-fit, the “circle of trust” wanted the big names. It became an uphill battle as every resulting tactic and associated spend was questioned. Think bigger! Go crazy! Ironically, the same words were said to Adam Neumann by Masayoshi Son of SoftBank following his $4.4 billion dollar investment. Ultimately, I surrendered, changed direction and left soon thereafter. The lack of progress in pursuit of prospective whales pushed me out the door.

It took Adam pushing WeWork near the brink of bankruptcy for him to be fired via a golden parachute worth hundreds of millions. At one point, WeWork was burning $100 million dollars PER WEEK and profitability seemed like a pipe dream. For most employees, it was too little too late. Thousands lost their jobs and their equity was worthless. 

The good news is, it appears that the “founder-friendly” investment sentiment is starting to change as valuations dramatically decline and the focus on profitability is once again a priority. According to a CEO study featured in the Harvard Business Review “founders add the most value as CEOs in the early years of a firm’s development, by the six-year mark (on average), they become more valuable in non-CEO positions, such as CTO or a board seat.” (December 2021).

If you’re looking for your next gig inside or outside of your company, beware of those that possess a vision and supporting charisma but lack experience. Be sure to talk to current AND former employees to understand the pros and cons of working for such an individual. Oftentimes, we get so excited about a new opportunity that we fail to do our own due diligence. We fear that negative feedback will prompt us to look elsewhere. Isn’t knowing now better than being surprised days, weeks or months after you’ve started? Nothing worse than being forced to reignite your job search because other opportunities have now passed. Finally, ask the recruiter about the turnover rate within the leadership team. Attrition is expected in the C-suite but if the door revolves every year, beware. Strategies never stick in such environments as they are quickly replaced by new blood, creating chaos amongst the ranks. 

I’m surprised and disappointed that no candidate has ever reached out to me to learn more about one of my former employers. Afraid of what they may learn? They shouldn’t be. My challenges may spell opportunity. My successes may be replicated. And, at the end of the day, I am just one datapoint. 

I wonder what venture capital firm Andreessen Horowitz learned during their due diligence of Adam Neumann’s latest real estate venture, Flow, before writing their largest single check of $350 million last year?

Confessions of a C-Suite Crybaby

I demand you to stop. Please, I’m begging you. What do you want from me!? Stop now and we’ll watch Marley & Me this weekend where you can run free. Promise! My tears ignored my desperate pleas as they continued the path down my cheek. They weaved their way through my make-up, taking my mascara along for the ride. My propensity - and ability - to control every other aspect of my life was completely lost on my H20 friends. “You don’t own us Kerri Pollard!” 

This wasn’t the time or place for a crybaby. I was a member of the C-suite and bawling my eyes out in the presence of my peers while sitting in a conference room surrounded by glass, which was positioned perfectly in the epicenter of our offices. “Come one, come all! I invite you to bear witness to a female exec weeping with abandon, proving our point that women really are ‘emotional!’ Check out Kerri the Crybaby before her tears decide to dry.” 

No, no one had died. Instead, the executive team was discussing pending layoffs in which the CEO kept reiterating that he didn’t trust any of us to execute them in a professional manner. Having been burned in the past, he feared that he would be the sole company villain during this super shitty exercise. The rest of us merely “messengers,” inferring that we would blame him - and only him - for this dire decision and fail to bear any personal accountability.

That’s it. Crybaby explained but not yet understood. 

Since I was the only one crying, I justified my tears with exhaustion excuses. I was also the newest member of the team, making significant personal sacrifices to possess a seat at the table. Losing the trust of the CEO in less than three months scared the shit of me. I felt my “badass” persona melting around me as my peers stared with pity, amusement and disappointment. I felt like a freak. The next day, the CEO apologized for bringing his baggage to the table, recognizing that this was a different team - with more experience than the last - and one that he could trust. 

Looking back, shame on me for failing to assess my own set of baggage. Why was I so triggered? I’m a passionate person, believing tears to be therapeutic. But, weeping at work because your CEO lost trust is drama with a capital “D.” It wasn’t the first time nor would it be the last that my waterworks emerged in front of my peers. It was time to understand the core issue of my crying. 

Being a female, first-born child of two educators in the 1970’s is the perfect recipe for creating a people pleaser and perfectionist. In school. At home. On the tennis court. Exceeding the expectations of others was an excellent source of self-esteem and I was extremely skilled at doing so. Being raised by parents that have a very high bar where satisfaction is a fleeting moment merely exacerbates this trait. I clocked my parents’ every move and mood so I could mold myself to win their affection. Who do you need me to be today!? 

Hello codependency, goodbye Kerri. 

According to Psychology Today, the clinical definition of a codependent is as follows: “Codependents (aka, givers) are self-critical and often perfectionistic; fixing or rescuing others makes them feel needed. They focus so much on pleasing others that they neglect their own wants and needs. Givers generally have low self-esteem, find it hard to set boundaries and be assertive, and struggle with asking for help when they need it. ‘Takers’ are often struggling with serious issues, such as emotional immaturity, mental health problems and addiction.” 

I know that I’m not the only one in the Codependent Club. 

When I first started playing tennis tournaments in middle school, our family would travel for hours through Wisconsin farmland to reach my competitive destination. If I lost in the first round, it was a quick and miserable turnaround. In one such tournament, I came out of the gate crushing the ball and ultimately, my opponent. No longer the underdog, the pressure to win began to build. My body started to stiffen; my right arm curled like that of a T-Rex; and my crushing forehands soon dissipated into weak lobs. My opponent started to crush me. Peering through the fence, my parents sat on their aluminum lawn chairs with arms crossed as if I had just told them that I was pregnant at 12. Feeling every ounce of their disappointment, I descended rapidly into defeat. 

In the two-hour drive home, no one spoke. No words of reassurance nor advice. The silent treatment is Kryptonite for codependents. I was physically and mentally alone in the back seat of our 1985 Chrysler LeBaron. Was I playing tennis for them or for me? Did I even like this damn sport? I didn’t know. What I did know is that I failed to meet their expectations and my self-esteem plummeted. 

We teach people how to treat us and I was an excellent teacher. Every CEO that I worked for morphed into my parents. I reverted to acting like a child as I sought their constant approval, recognition and crying when I failed to do so. Putting my career first, I possessed no boundaries so I could perform every task to perfection. Fly to New York tomorrow and miss my daughter’s birthday. Absolutely! Assume our European remit with no increase in pay. Okay! Obsess 24/7 about mistakes made or problems brewing and not be present for your family. That’s me! 

I was operating in a constant state of anxiety in fear of disappointing others and if unsuccessful, I would be relegated to the backseat…alone. I retired at the early age of 49 because I was exhausted. Being an approval junkie generated much career success but it came at a cost. Me. I’m extremely thankful for the privilege of time to find 12-year-old Kerri, give her a hug and rediscover healthier sources of self-esteem. I’m still a crybaby but my H20 friends have been assigned to global events and of course, dog rescue clips on TikTok. The tennis racquet has been replaced by a pickleball paddle. No history. No baggage. Free of expectation and full of fun. What a concept!

My daughter recently entered corporate America via her college-sponsored co-op and my hope is that she remains her biggest fan. I hope she can trust her own abilities and amazing work ethic. Understand the source of her own triggers and how to effectively manage them in the moment. Celebrate her own accomplishments vs. waiting for recognition from others. Cry when needed and move on. Most importantly, I hope she remembers the quote that I shared with her years ago from Mohadesa Najumi, “the woman who does not require validation from anyone is the most feared individual on the planet.” 

The Many Faces of Elizabeth Holmes and Me

Four-inch heels on a 5’9” frame, a red sole serving as the lone color in a sea of black fabric. Platinum faux hawk with a dark splash of color, accenting its peak, finished with shaved sides and a razored nape. Skinny dark jeans topped with Helmut Lang’s latest trend, peeking out beneath the omnipresent leather jacket. Adolescent nickname of “pizza face” prompting full-coverage foundation and all of its fixings, topped with a cherry of red lipstick. 

Looking like the singer Pink went corporate, me and my body armor made a statement at every meeting attended while President of CJ Affiliate. In my retired state, I have regressed back to my inner child, strutting harem-inspired sweatpants, high tops and a baseball hat, a crown to my now chest length hair. This aging face bears nothing more than a tinted sunscreen and little lip gloss. 

From rock chic to casual athlete. But, who was that Mohawk Mama and why!? 

In a New York Times interview with Elizabeth Holmes, former CEO and founder of Theranos, written prior to the start of her 11-year sentence for investor fraud, the reporter repeats the rumor that “Jennifer Lawrence had pulled out of portraying her in a movie.” Without missing a beat, Elizabeth states “they’re not playing me. They’re playing a character I created.” The reporter then asks, “so why did she (Elizabeth) create that public persona?’ in which Elizabeth responds, ‘I believed it would be how I would be good at business and taken seriously and not taken as a little girl or a girl who didn’t have good technical ideas.’”  

A Stanford dropout, Elizabeth was 19-years-old when she started Theranos. 

Steve Jobs-esque black turtleneck, Kabuki red lipstick accompanied by a “throaty contralto” were the critical components of Elizabeth’s body armor. One could argue that it worked. In 2013, Elizabeth was worth $4.5B and trumpeted as the youngest self-made billionaire. With a company valuation of $9B, Theranos’ investors and board members included such famous folks as media mogul Rupert Murdoch; Oracle CEO Larry Ellison; two former U.S. Secretary of States, Henry Kissinger and George Shultz; and the former CEO of Wells Fargo, Richard Kovacevich. 

Don’t get me started on the lack of board accountability and responsibility for Theranos’ demise. 

Did 19-year-old Mark Zuckerberg also ponder what he could do to be taken more seriously as a young entrepreneur? As evidenced by “Hoodiegate” in 2012 when he was courting investors in a black hooded sweatshirt, I doubt it. At the time, a Wall Street analyst stated the following on Bloomberg TV: “I think that’s a mark of immaturity. I think that he has to realize he’s bringing investors in as a new constituency right now, and I think he’s got to show them the respect that they deserve because he’s asking them for their money.” 

Silicon Valley laughed, “....he’s going to build a $100 billion dollar business and change the world? That’s what the hoodie signifies? Well then, I think that he shouldn’t take it off at all costs!” (Alex Wilhelm, The Next Web, May 2012). 

Facebook reached its highest valuation of $1 trillion in September 2021. 

There are hundreds of articles instructing women on how to be taken more seriously in the workplace. The themes are all disgustingly the same: Be over prepared; develop your voice; find allies; be persistent; nail your body language; and push back when necessary. I think of the hours spent in front of the mirror practicing presentations, whether the audience was one or 1,000. Did my male counterparts do the same? As women, do we not trust that the merits of an idea can stand alone? Why do we feel the need to sell it, both physically and emotionally? 

In speaking with my friend Tim, I asked about his process as an enterprise account executive when trying to earn the respect of the audience before him. While at the same company, we did dozens of client pitches together and apart. In so many words, he asked, “what process?” Tim did confess that when a woman is holding court, a man’s initial reaction is to assess her level of attractiveness (thank you testosterone). The mature male will move on quickly and focus on the business at hand. The immature one may not, making her appearance a potential factor in his decision-making process. Knowing this, some women may use their physical prowess to advance their agenda. 

What if the script was flipped and women were the majority in most board rooms? One would also have to dream that we lived in a matriarchy, not a patriarchy. Welcome to Barbieland! Would my friend Paul be forced to develop a “process” to secure credibility in an estrogen-dominated environment? Would those instructional articles read the same - i.e., be over prepared, etc? 

Perhaps. 

Regardless of gender, do what YOU need to do to feel confident. As Lyndon B. Johnson once said, “conviction convinces.” Over prepare or be off the cuff. Wear red lipstick or cherry chapstick. Adorn a hooded sweatshirt or haute couture. Slip on heels or sneakers. Form alliances or let them happen organically. You do you. One can’t control the reaction of others so create a process and persona that inspires you to do your best work. Let’s not forget that Mark’s pitch while wearing an “immature” hoodie had IPO investors fighting for his business. 

Despite your conviction, there may be rooms in which securing the respect of others may seem futile as they are controlled by the likes of Succession’s Logan Roy. My tendency is to assume the blame. I’m not communicating effectively. Or, my goals, values or priorities are not aligned. Their response - or lack thereof - is triggering my own trauma. It could be those things but what if it’s not? If you feel like you are the victim of conscious/unconscious bias or sexism in any form, I encourage you to find a different “room” or consult a lawyer. I recognize that both these options originate from a place of privilege and require much bravery. Lacking such strength, I still regret not exploring legal action at a critical juncture in my career. 

Whatever you do, do NOT create a character like Elizabeth Holmes in your journey for credibility. In the words of author and coach Jay Shetty, “every time you try to change yourself to get someone to like you, you lose a part of yourself.” Elizabeth lied to herself and ultimately to all those around her, landing her in a Texas minimum security prison. 

Mohawk Mama wasn’t a character. It was me. Mohawks and sweatpants are two sides of the same Kerri coin. Both personas were and are authentic. That mohawk won a lot of business during my career and the sweatpants are killing it on the pickleball court. ;) 

got fired?

I should have seen it coming. Exclusion from meetings. Taking the long way to avoid my personal perimeter of engagement. No eye contact, despite my desperate attempts to make a connection with my green ones. For weeks, I had been feeling isolated, invisible and very insecure. 

Prior to the arrival of most that morning, I was pulled into a corner conference room by our co-founder. Perpetuating the no eye contact trend and adding a nervous twitch, he sputtered that the company had “made the difficult decision” to eliminate the chief revenue officer (CRO) position and ultimately, me. Having worked at another company for 16 years, I was stunned. “Was there anything that I could have done differently,” I asked. With tears in his eyes, he shook his head side-to-side, prompting my own waterworks. 

The rest of the conversation is a blur as we both struggled to communicate but it was made clear that I was to leave immediately. Why? I don’t know. Since I entered the workforce at 15, my professionalism nor performance had ever been called into question. If I were to remain on-site days/weeks, my belief and positivity in the business would not wane, allowing for a graceful exit. Inexperience was the only reason that I could conjure in order to sympathize with their approach. The awkwardness of that infamous day lives on for all involved as we haven’t spoken since. 

Given the immediacy, I sprinted back to my desk in an attempt to mitigate the size of the surrounding audience. With every minute, more bodies entered the building with a Philz coffee in hand, clueless to the conversation that had just ensued. Fueled by shame, my “flight” mode was in full effect, boxing my belongings like I was trying to achieve a Guinness world record. Once complete, I slid out in silence and drove home to the arms of my husband where the waterworks would come and go, depending on the memory. 

Unlike the recent Twitter firings, my access to Slack remained active for several hours following so I possessed a rare insight into the narrative surrounding my departure: “Today is Kerri Pollard’s last day. Kerri is an exceptional talent that we are fortunate to have had join us for the ride. Unfortunately, her unique skills are not ones that we will require going forward so her position is being eliminated and will not be backfilled.” 

According to Zippia, an online recruitment service, 40% of Americans have been fired from a job. In 2022 alone, 15.4 million Americans were laid off. As proven by the numbers, getting fired is a rite of passage for A LOT of people. So, why did I feel so much shame? Word of my elimination was already dancing from ear to ear but shame prompted me to ask our CEO to massage the narrative to a “mutually agreed-upon” separation. The lyrics didn’t change and the song kept playing, as is. 

In an upcoming post, I will speak to my childhood and the baggage born in Green Bay, WI. Rarely feeling “good enough” is one of my largest pieces of luggage, especially in the presence of those on a pedestal, elevated by yours truly - i.e., bosses, Ivy-educated, parents, etc. Getting fired was the ultimate slap of validation, cementing this insecure mindset for years to come. I was convinced that when others learned of this “slap,” no one would want to hire or work with me. “She’s not xxxx enough.” Pick an adjective as I exhausted all of them in the exercise of self sabotage. 

Good news for all, my perspective is dead wrong. I recommend an alternative one as outlined by Harvard Business Review: “Most leaders see an executive in the ranks—even the best performers—as filling an assignment. When it’s over—for strategic or financial reasons—so is the executive’s tenure with the company. Even the most desirable job is finite.” (July - August 2001). 

“Filling an assignment.” Executive or not. Fired or not. Most jobs should be considered an assignment that will come to an end. Nothing more. Your colleagues are not family. The company is not your forever home. Your job and identity are not the same (Kerri Pollard). The “assignment” may change during the course of your tenure, requiring a different skill set. Or, a new manager with opposite expectations may assume the helm. Or, like mine, your assignment may be eliminated in its entirety. 

The power surrounding the word “assignment” pales in comparison to that of career, job, profession, etc. It does not have the strength to tell any of us that we are “not good enough.” 

With an assignment mindset, what are you doing NOW to land your next one? Always be connecting. Shout out to my former colleague Scott and his commitment to reaching out to a sub-set of friends and past co-workers every Sunday night. No favors asked, merely a “hello” and “how are you doing? What can I do to help you?” Speaking of, I owe you a return phone call! Thank you George for encouraging me to interview for a new “assignment” at least once a year. My apologies in that I failed to explore other industry associations or non-profits, like you also recommended. In short, readers do as I say, not as I do. ;)

Although I’m no longer interviewing, I still get asked, “why did you leave?” With my head held high and shoulders back, I state with pride, “my assignment came to end.” I didn’t know it then but it ended up being the BEST outcome.