Missed paychecks, careers damaged, hearts broken

Hot Air Balloons & Sales - More In Common Than You Think

What do a hot air balloon ride in Cappadocia, Turkey, and sales have in common? At first glance, you'll likely say nothing at all. I sure did. But, reflecting from 1,000 meters in the sky, I realized there is much more in common than I thought. It's funny actually; 've spent the past 21 days traveling and have found more parallels to sales than I would have ever imagined. Not sure if that makes me keenly aware of my surroundings and deeply introspective, or if it means I need to get much better at shutting off my work brain. Likely a little bit of both.

If you haven't taken a hot air balloon ride, you're missing out. It's one of the most serene yet exhilarating things you can experience. Easilly a top-5 life experience for me. There's a fascinating parallel between this adventure and the world of sales. Both realms require a deep commitment to process, an understanding of conditions, and an ability to adapt—all crucial elements that determine the journey's success or failure.

Meticulous Preparation: The Launchpad for Success

Before a hot air balloon graces the sky, there's meticulous preparation behind the scenes. Balloonists must check the balloon's integrity, fuel levels, and weather conditions. Similarly, in sales, the groundwork is just as critical. Sales professionals craft their approach with precision, research their prospects thoroughly, and set the stage meticulously for their interactions. This preparation is the launchpad for success, setting the tone for the journey ahead. Skipping one of these steps ballooning can be catastrophic. Skipping steps in sales can be catastrophic to your deals.

Timing and Conditions: The Crucial Elements of Takeoff

In ballooning, launching at the wrong time or in unfavorable weather can result in an uncontrolled and risky journey. In Cappadocia, the Turkey Civil Aviation Department has an office that monitors the weather in real-time, letting balloon companies know each morning 20 minutes before take-off is scheduled if they can fly or not. Thousands of people each year wake up at 4 am only to find out at 5:45 that they cannot fly. This goes on for days until the weather is suitable, or it's time to leave the city. The same goes for sales. Understanding the market's climate, recognizing the optimal timing for your pitch, and gauging the prospect's readiness is akin to reading the weather before a balloon flight. This awareness and timing ensure a smoother ascent towards your goals. If you don't take the time to deeply understand your prospect's pain, tie your product to deep needs, and show a positive ROI, you'll find your deal unable to take off as well.

Adaptability: Navigating the Winds of Change

Once airborne, a balloon pilot must constantly read and adapt to the winds, changing altitude to find favorable currents. Fun fact: There is no steering on hot air balloons. The pilot has no idea where they are going to land. They can control altitude, but not direction. There's a ground team following the balloons (up to 140 of them) all over the city in vans waiting for landing. In the world of sales, the ability to pivot strategies based on customer feedback, market trends, and evolving needs is equally vital. This adaptability ensures that you're not just moving but advancing in the right direction, turning potential challenges into opportunities for growth.

The Ascent: A Blend of Anxiety and Excitement

The initial lift-off in a hot air balloon is a blend of anxiety and excitement, a feeling that many sales professionals can relate to when a prospect first shows interest. Let me tell you, I was scared $h!tless before we were up in the air. It's a critical moment where the culmination of preparation and opportunity meet, propelling you upward. This phase is thrilling, filled with anticipation of what the journey might unveil.

The View from the Top: Reflecting on Achievements

Reaching the peak altitude in a balloon ride offers unparalleled views, a moment of awe that mirrors the satisfaction of closing a deal in sales. Both experiences provide a unique perspective, offering insights and learnings that enrich you for future endeavors. They remind us that while the destination is rewarding, the journey's lessons are invaluable.

Whether you're navigating the skies in a balloon or steering through the complexities of a sales cycle, the essence lies in embracing the process. It's about understanding that success is not just about reaching the destination but also about how you adapt, learn, and grow throughout the journey. So, as you chart your course in sales or prepare for that awe-inspiring balloon ride, remember that the beauty of the journey lies in its unfolding – one meticulous, adaptive, and exhilarating step at a time.

Lessons Learned as a Fractional GTM Leader

Each week in this section, we aim to bring you real-life lessons learned either by us or by one of the founders we work with. All names have been changed to protect the identities of others...

When Payroll Doesn't Get Paid and Dreams Get Crushed

Startups are known for volatility. After working for (and with) dozens of them, one thing I've learned is certain. Uncertainty.

In the early days, there is usually angst around the product being good enough, deals closing fast enough, and if there is enough funding/runway to hit the next milestone. All of this is to be expected, and if the founder is a solid person, explained to early-stage employees during the interview process. Those of us who have "been there, done that" with multiple startups before know the right questions to ask to root out misinformation, and how to work the backward math to validate these answers. If the math doesn't add up, it's time to run (not walk) in the other direction. Sometimes though, people aren't so lucky. This, despite asking all the right questions, and seemingly getting all the right answers.

Startups represent a vibrant yet volatile world. This is the saga of "Michah," who was new to the startup world and excited to get her first gig as an Account Executive with "CharskiTech." This is one of the more frustrating stories I've heard recently and particularly stands out as a stark lesson in the perils of miscommunication and misplaced trust. Michah was bright, committed, and hungry. She believed she and her co-workers were on the cusp of something incredible. Michah was drawn to CharskiTech by a charismatic founder, "Chelsea" who spoke passionately about innovation, growth, and the promise of substantial future rewards. Chelsea was a multi-time founder which quickly earned her more trust with those looking to join the team. Chelsea used stories of past success to earn people's trust.

During the interview process, Chelsea told Michah of almost $3M in ARR on the books. Until recently, this was done via founder-led sales. A few months ago Chelsea hired John as CharskiTech's sales leader, and now they needed a few account executives. Now was the right time to transition to a full-time sales team as Chelsea needed to focus her efforts on securing the next round of funding. Despite a seemingly healthy ARR, the need for additional funding was urgent, as the burn rate was substantial. This gave MIchah a slight pause during the hiring process as some of her trusted peers saw red flags. Michah was willing to overlook these flags as Chelsea seemingly had all the right answers. On top of this, the product appeared to be exceptional. Solving real problems that those working for CharskiTech had heard time and time again. Couple that with a very public group of well-respected "advisors" this seemed like a startup gig that could be the real deal.

However, beneath the surface, a troubling reality lurked. Despite Chelsea's assurances of financial health and a bright future, CharskiTech was hemorrhaging money. The burn was actually substantially higher than what was represented. How though? There was so much GTM/Tech debt that had been built by Chelsea doing things the wrong way over the past year and a half that expenses were out of control. Failed expensive hires that didn't work out. Costing valuable time and money. Tech decisions were made that were far too advanced for a company in this stage of growth with contracts signed that could not be gotten out of. Most shockingly though was the $3M in ARR that Chelsea had so happily bragged about during the interview process? Yeah, not the real number. Upon further digging, Michah and those hired along with her were able to uncover the real number was sub $1M. But why would Chelsea lie about this? Unfortunately, no one knows. Because, as the story unfolded Chelsea was nowhere to be seen other than the occasional Teams message telling employees all would be okay, and that this "is what startup life is like."

The first shockwave hit when the company missed payroll for the first time. Confusion and concern rippled through the team, but Chelsea's reassurance framed it as a mere hiccup, a test of their commitment to the cause. The bank simply missed a deposit. "This can happen when you are a startup" Chelsea said. Assuring the team this would not happen again, Chelsea said the funds would be in the bank long before the next pay period, and that all employees would be made whole.

When payroll was missed a second time, concern escalated to alarm. Chelsea's response was dismissive and cavalier: "This is nothing. This is how startups work. If you want to be rich, you need to be willing to sacrifice a paycheck or two." This statement, meant to rally the troops, instead sowed seeds of doubt and resentment. You see, founders usually have a much better financial situation than those on the team. While they may be able to miss a check or two, those on the team can't. Chelsea, struggling to pay her bills already was lost and confused. She was scared and confused and did not know what to do. She had just gotten divorced, lived in her home with her 6-year-old son, and had just missed her mortgage and car payments. She didn't have a ton of runway in the bank and thought CharskiTech was her ticket to independence.

The impact on the rest of the team was profound and multifaceted. Financial strain tightened its grip, forcing some to deplete their savings, while others struggled to pay bills or support their families. The stress bled into their personal lives, straining relationships and eroding their mental health. The once tight-knit team frayed as trust in Chelsea and the company's leadership evaporated.

Beyond the immediate financial turmoil, the experience left deeper scars. Employees began to question the ethics of startup culture and their place within it. The promise of startups as meritocracies, where hard work and dedication lead to success, was tarnished, and replaced by a narrative of exploitation and disillusionment. Ultimately, the paychecks never came. The story about additional money was fiction. Chelsea was desperately working to secure funding because she was out of money, and didn't have the ARR to support a true raise. She wasn't honest with her employees as she thought if they could close deals fast enough, and she could somehow raise more money quickly enough, that all would be well in the world.

Sadly, all didn't end well. Michah never got her two paychecks. Neither did the other team members. Chelsea never raised an additional round, and a once-promising startup quietly slipped into the darkness. No one dared to say a word publicly because if they did, they feared they'd never get a job at a startup again. You see, despite this... their hope was not broken. They desperately wanted to help build something special. The next great thing. The next amazing startup.

This story serves as a cautionary tale for both founders and employees in the startup ecosystem. Founders must prioritize transparency and honesty, recognizing that their team's trust is a currency as valuable as any capital investment. Employees, in turn, are reminded of the importance of vigilance and due diligence, ensuring they align with organizations that respect their contributions and well-being. We often use the term "show me the receipts" when talking about hiring leaders. This is another way of saying; "Show me the proof. Show me what you've done and how you've done it." Employees should not be afraid to ask for the "receipts" when interviewing. Validate the metrics. Verify the ARR. Make sure you aren't being sold a story. While this doesn't in any way guarantee a positive outcome, it certainly reduces your risk. If you need help phrasing these questions in a way that doesn't come off as offensive, drop me an email... I'm happy to help.

CharskiTechs journey underscores a fundamental truth in the startup world: success is not solely measured by market disruption or valuation but also by the integrity and ethical standards upheld on the path to innovation.

Content We Can't Get Enough Of

I've been a huge fan of Dale Dupree and The Sales Rebellion for some time. His out of the box thinking has helped hundreds, if not thousands of sellers stand out from the crowd in an authentic way.

When he called out the absolute ridiculousness of the below job description I could not help but make this my content share for the week. Go give Dale a follow.