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The loneliness of leading a cybersecurity startup | #hacking | #cybersecurity | #infosec | #comptia | #pentest | #ransomware


Linor spends her days working with cybersecurity founders at her Venture Capital firm. Gaining insight into their experiences over the course of building these relationships and supporting the brick-laying of their visions, she shares observations on the tough – and often undiscussed –impact their startup journey has on emotional wellness and self-care.

The world of well-invested startups is a glamorous beacon to highly motivated entrepreneurs across the cybersecurity industry, and the ultimate responsibility for reaching the mark lies with the good management of the Chief Executive Officer. Hungry for success and set – often to the point of obsession – on building something big, these leaders forge ahead with millions in funding on the line.

However, this determination alone is hardly enough to contend with the true reality of executive leadership; as VP of HR with the opportunity to frequently meet the Israeli tech sector’s best and brightest, I’ve come to appreciate how emotional resilience is no less important than passion, technical knowhow or business acumen. It takes a particular kind of mental fortitude to persevere when the buck stops at you. Surely, leading a cybersecurity startup is one of the loneliest jobs in the world.

My goal is hardly to discourage ambitious technologists from making our digital lives safer. However, it is critical to acknowledge the difficulties these founders face – especially as we move from cybersecurity’s gold rush era to one of more austerity. In a thankfully developing culture of openness around wellness and mental health, we can direct this knowledge towards offering better support and preparedness to cybersecurity company leaders.

In this spirit, I sat down with successful cybersecurity founders at different points of their company-building and scaling journeys to gain insight into their subjective experiences of carrying the weight of their companies on their shoulders.

Navigating the unknown

Few people draw as much admiration and bewilderment from our investment team as the aspiring company leaders we meet. With every signed term sheet, entrepreneurs commit themselves to endless herculean labors without an established roadmap for navigating its highs and inevitable lows.

When building something unprecedented and game-changing, the course and rules are steeped in darkness and uncertainty, with naysayers, critics, board members, competitors and time itself hurling criticisms every step of the way. Why on earth would anyone subject themselves to that?

Perhaps it should be made clear that, for most of the aspiring CEOs I meet, their career path is hardly a choice. Entrepreneurship often runs in their blood, serving as a defining force for the people who pursue it. This all-consuming nature has become a necessary qualifier for most investors; It’s an important tool for survival, as well as for success. This is not to discount the absolute necessity of vision, inspiration and faith in a good idea. But on the long road to entrepreneurial success, these are often subject to so much scrutiny and judgement that a different strength is necessary to stay the course.

These days, tightening budgets and dreaded potential layoffs only add to the pressure they feel. However, during the toughest times, an entrepreneur’s hunger to build can provide the critical momentum they need to move forward. Success often hinges on pure grit, and this grit can come at its own emotional cost.

Putting on a face

For many founders, their main sense of isolation lies in a duty to appear as a reliable and unshakeable pillar of strength that inspires investor funding and employee loyalty. This includes all successes and failures, regardless of how much direct control they may feel over them, and is quite a challenge for a community of people who represent the zenith of imposter syndrome. There is little as humbling as walking into a room where jobs are hinged on your decision-making. How is one to project confidence when navigating a wider fear of letting others down, as well as the unknown of what is to come?

Many founders are isolated by the seeming impossibility of the task they have promised to carry out. Building a company at the pace of a startup is like trying to defy the laws of physics, demanding that founders grow something from nothing in record time in an increasingly competitive market. Superhero expectations have these CEOs building and selling, marketing, hiring and raising more money simultaneously. It’s no wonder, then, that no matter how much founders tend to achieve, they hardly ever feel as though they have done enough. With the pressure of such expectations on their shoulders, successes can feel hollow on the constant chase for more.

Facing constant scrutiny

Most critically, few CEOs have peers they can truly relate their experiences to or compare benchmarks and marinate in their success with. Given the unique path of every company journey, comparing milestones reached at face value can result in a misleading sense of either inferiority or inflated success. Press releases touting new funding rounds or partnerships of competitors only tell half the story. The struggle, toil and negotiations required to reach such points behind closed doors almost always go undisclosed. It is an incredible strain to have to rely on such tiny snippets of information – lacking so much in context – to set as comparative benchmarks for success. This is worsened by the data-overload that plagues anyone responsible for managing everything, as well as the constant measurement to which they are subjected by investors and the media.

There is no cure-all for these struggles. However, it is possible for fellow stakeholders to help more. As value-add reaches new heights among VCs, we have a responsibility to understand how we can offer better support for founder wellness and emotional resilience.

As investors who generate in-house services and accelerate growth for these founders, we do, at the very least, offer hands-on support and guidance across different company-building responsibilities. This can help relieve some of the pressure company founders face and (more importantly) help them feel slightly less alone. Moreover, offering in-house experts on business development, operations and particular product sectors can help illuminate their paths and enable them to focus their business-building efforts on areas that leave them more fulfilled.

Sharing responsibilities

VCs and investors must also appreciate how their conduct can contribute to CEO isolation. Again, fellow cynics might argue that a business partner’s mental health is quite literally nobody’s business. However, perhaps we should see ourselves as stakeholders in a founder’s wellbeing.

Why not foster more confidence in our founders with proper coaching and ensuring a safe environment for discussion? This can only encourage more transparency and catch potential issues at a more manageable point in time. For example, CEOs have long called for a judgment-free zone where they are spoken to as true partners by investors. A dynamic of board meetings that put founders on the spot only adds to their isolation and desire to master problem-solving on their own instead of sharing it. Collaborative board discussions create equality between the members of the board and founders, as well as more potential to offload problems to those best equipped to handle them.

Finally, VCs can leverage their powerful networks and resources to help find true mentors, coaches and other forms of wellness support for their founders. A mentor, specifically someone who has led a company in a similar sector, can be one of the strongest sources of support for CEOs across their company lifecycle. This is especially relevant for promoting better work-life balance and stress-management skills. Mentors are most likely to appreciate the toll leadership can take on the overall health of founders, who, under so much stress, often sacrifice things like eating well, sleeping well, family time and investing in personal growth.

It is worth noting that this type of stress, loneliness and isolation occurs mostly with first-time founders. By an entrepreneur’s second–and surely by their third–venture, mistakes weigh less, and the bigger picture is far more readily accessible. However, to get entrepreneurs to this point in the best mental shape, VCs can strive to do much more to both understand and address the emotional stumbling blocks of company-building.

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