Final Boss: Failure – A Hard Look at What It Means to Fall, Learn, and Rise Again

Boston New Technology’s Virtual Tech Week concluded with an event that will be remembered for a long time to come. Final Boss: Failure. Our industry glorifies the highs and buries the lows, and this session aimed to dissect failure with unflinching honesty. The discussion was not a celebration of failure, nor was it an exercise in pessimism. It was an attempt to reframe what failure means for founders, operators, and investors alike.

Failure: The Startup Industry’s Most Misunderstood Concept

The conversation opened with a simple but pressing question: Do we truly understand failure? The answer, as it turns out, is complicated. Failure in the startup ecosystem has long been packaged into neat soundbites—fail fast, fail forward, and other well-worn phrases that often lack substance. But for those who have actually lived through it, failure is rarely neat. It is painful, costly, and often unpredictable.

Steve Vilkas , who led the discussion, shared his personal journey with failure, recalling past ventures that did not scale as expected. Rather than framing these as losses, he emphasized how they served as pivot points—forcing him to develop self-efficacy, sharpen his situational awareness, and gain the clarity needed to make better decisions.

Steve’s Thesis on Navigating Failure: Clarity, Self-Efficacy, and Situational Awareness

Steve Vilkas laid out a structured approach to dealing with failure, centered on three critical pillars: Clarity, Self-Efficacy, and Situational Awareness. Each of these concepts functions as a key to not just enduring failure, but using it to transform both the founder and the company.

1. Clarity: The Starting Point for Recovery and Growth

Vilkas argued that founders often struggle with failure because they lack clarity—not just about their vision, but about the reality of their situation. Clarity is the ability to see failure for what it is: a symptom of deeper challenges, not the problem itself.

• “In order to do anything, you have to have clarity. You have to know what you want to do, why you want to do it, and with whom you want to do it.”
• Without clarity, founders are prone to react emotionally to failure rather than analyzing it systematically.
• Clarity means defining failure in practical terms: Was the market wrong? Was execution poor? Were the right people in place? Rather than seeing failure as a personal indictment, clarity helps break it down into solvable components.

2. Self-Efficacy: The Skillset to Rebuild from Failure

The second pillar, self-efficacy, is about cultivating confidence in one’s ability to recover from failure. Steve credited his mentor at Prepare 4 VC, Christopher R. Dube , with helping him understand that failure only defines you if you allow it to.

• “Self-efficacy enables me to have a better understanding of what I’m good at, what I’m not good at, and how not to punish myself for those deficiencies, but rather to develop mastery.”
• Self-efficacy is not blind confidence—it is measured adaptability. A founder with strong self-efficacy does not spiral into self-doubt but seeks mastery over weaknesses.
• Founders who fail often fall into two camps: (1) Those who internalize failure and stagnate (2) Those who analyze failure and adapt The latter is what separates resilient entrepreneurs from those who give up.

A crucial insight here is that self-efficacy must be cultivated before failure happens, so that when it inevitably does, the founder is prepared to handle it without emotional paralysis.

3. Situational Awareness: Understanding the External and Internal Landscape

Failure does not happen in a vacuum, and situational awareness ensures that founders can interpret the factors that contributed to failure. According to Steve, one of the biggest mistakes founders make is failing to read the room—whether that’s in fundraising, hiring, or market positioning.

• “You have to be able to read the room and protect yourself, but you also have to leave yourself open to opportunities. It’s a very complicated thing, as we know.”
• This applies to relationships with investors, advisors, and the market itself. Founders who lack situational awareness often repeat the same mistakes because they are blind to external feedback.
• Example: A startup that fails due to poor product-market fit should not blame “bad luck” but rather dissect whether they ignored warning signs from customers, investors, or competitors.

By being highly attuned to the broader landscape, founders can fail faster and smarter, using each setback as a data point rather than a personal defeat.

Conclusion: A Framework for Failure that Leads to Transformation

Rather than seeing failure as an endpoint, Steve framed it as a structured opportunity for transformation. His approach suggests that failure should be broken down into three essential questions:

1. Clarity: Do I understand why I failed, or am I reacting emotionally?
2. Self-Efficacy: Do I believe in my ability to adapt and rebuild, or am I stuck in self-doubt?
3. Situational Awareness: Did I misread the market, my team, or my investors? What external forces contributed to this outcome?

This thesis provides a playbook for failure recovery, moving beyond generic startup slogans (“fail fast”) and into a practical, strategic framework for founders facing adversity.

Failure is not a mark of incompetence. It is, in Steve’s words, “a pivot point—one that either sends you forward or leaves you stuck. The choice is yours.”

“A failure can sometimes just be a pivot point. Actually, I would argue that most failures are pivot points because they pivot us in a direction that we’re ultimately destined to go..."

Tawanda Mahachi built on this, offering a stark assessment of fear in the startup world. Fear of rejection. Fear of wasted effort. Fear of putting something into the world only to watch it crumble. His message was clear: Lean into discomfort.

“Whenever you feel uncomfortable in terms of learning challenges and growth opportunities, lean into the discomfort because chances are that’s probably where you should be going..."

The greatest mistake founders make is waiting too long to act because they are afraid of what happens if they fail. Tawanda also warned against excessive planning without execution. While planning is necessary, too much of it becomes a self-imposed paralysis, preventing progress. He intimated; "Honestly? Part of all this, you know, if I was to look at it in retrospect in my own failures, other people’s failures that I’ve worked with, is this sort of excessive planning and little action.”

• He encouraged founders to prioritize bias toward action, emphasizing that true learning only happens when something is put into motion.

Finally, concurring with Steve's emphasis on clarity, self-efficacy, and situational awareness -- Tawanda’s remarks spoke to the need for self-awareness. Many founders convince themselves they can do everything on their own or resist sharing equity, only to realize too late that a lack of support hinders execution He suggested: “Be honest about what you can do. Because oftentimes as founders, we are like, we can do it all, right? But execution steps are a little fuzzy. That’s where a lot of folks stumble. Surround yourself with the right people, even those who may not share your risk tolerance. "

He noted that some individuals who avoid startups for stability reasons can still offer valuable insights and expertise.

Shweta Agrawal took the conversation further, challenging the binary thinking of failure versus success. If you are not failing, she argued, you are not learning. Growth is not about avoiding failure; it is about failing intelligently—identifying what does not work and iterating faster than the competition.

“If someone is not failing every day or multiple times, they’re not making progress. If you’re not failing, if you’re not making mistakes, that means you’re not even trying something out"

The Hidden Risks in Startup Failure: Investor Relationships and Execution Blunders

One of the most striking moments came when the discussion turned to investor relationships. Alex Martineau voiced a fear that many founders share but rarely say out loud, demonstrating his courage:

What if I lose someone else’s money?

It was here that the conversation took an unexpected turn.

Mahachi and Jason Kraus reframed the concern, explaining that investors do not expect perfection, but they do expect transparency. A startup’s failure is far more damaging when communication breaks down, when founders paint an unrealistic picture of success until the situation becomes unsalvageable. The worst thing a founder can do is obscure the truth from their investors.

In contrast, those who openly acknowledge risks, setbacks, and lessons learned are far more likely to retain credibility and future opportunities. “If you are honest, if you’re operating in good faith, and you’re keeping your investors informed, that is far better than keeping quiet and then delivering bad news all at once,” Tawanda explained.

The Difference Between "Fail Fast" and "Fail Forward, Transform Fast"

During Final Boss: Failure, the discussion drew a critical distinction between "fail fast" and the more intentional approach of "fail forward, transform fast". The former, while widely popularized in startup culture, often lacks the strategic depth necessary for meaningful growth. The latter reframes failure as a tool for active transformation rather than just an iterative process.

1. "Fail Fast" – The Problem with Surface-Level Learning

The fail fast mantra has become a startup cliché, often misinterpreted as an endorsement of rapid trial and error without sufficient analysis. While its core idea—moving quickly and learning from mistakes—has merit, it is often executed poorly.

• Founders pivot too often without real insight, mistaking movement for progress.
• It encourages an unhealthy tolerance for failure without accountability or deep learning.
• Speed is prioritized over strategic reflection, leading to repeated mistakes rather than smarter execution.
• Many founders fail fast, but they don’t extract valuable lessons before jumping to the next idea.

Eric Dubliner: The Hidden Gem

Eric Dubiner may not have been the loudest voice in the discussion, but his contributions struck a chord with those paying attention. While much of the conversation focused on execution, investor relations, and personal resilience, Eric provided a pragmatic yet deeply introspective take on failure, especially from an operations and leadership perspective.

The Emotional Discipline of Failure

Unlike the more sensationalized stories of startup flameouts, Eric focused on a less-discussed but equally dangerous failure mode—letting emotions dictate decision-making.

• “The thing I’d add to the list of gotchas is not to let emotions get in the way. Because it’s so easy—this is your baby, and you hold on to it tight… and you don’t see the forest for the trees.”

He pointed out that founders often become too emotionally entangled in their ventures, leading them to ignore clear warning signs or resist necessary pivots. His advice? Learn to detach. Not in a way that eliminates passion, but in a way that ensures decision-making remains rational.

The Startup Rollercoaster—Prepare for the Highs and Lows

Eric described the emotional volatility of startup life as a cycle that must be managed, not avoided:

• “The highs are going to be really high. The lows are going to be really low. And they’re going to come about 15 minutes apart. You’ve got to learn how to surf that wave without driving yourself and the people around you too crazy.”

This is a sharp contrast to the glorified hustle culture that romanticizes the chaos of startup life. Instead of glamorizing the grind, Eric advocated for emotional regulation, self-awareness, and strategic resilience.

Internalizing Failure the Right Way

Eric resonated with the idea that failure is not inherently bad—what matters is how quickly and effectively you internalize it.

• “Failure is not a failure. It all depends on how quickly you can internalize it.”

This perspective aligns with the idea that learning from failure is a skill in itself. Some founders take years to process failure, while others bounce back rapidly because they know how to extract key lessons and move forward without emotional baggage.

Is the Tech Industry Ready to Get Real About Failure?

This discussion left us with an unavoidable question: Is the startup world finally prepared to confront failure honestly? The answer is both yes and no.

On one hand, we see founders, investors, and operators becoming more open about past failures. Mental health in entrepreneurship is no longer an afterthought, and the illusion of overnight success is fading. Organizations like BNT are helping to normalize these conversations, making room for founders to engage with failure in a productive way.

Yet, in many corners of the industry, the stigma remains. Founders still hesitate to acknowledge setbacks until they have a redemption story. Accelerators and VCs still prioritize rapid scaling over sustainable growth. And the broader ecosystem still rewards those who maintain the appearance of success rather than those who demonstrate resilience in the face of failure.

The Path Forward: How We Change the Narrative

If we want to create a more realistic and productive relationship with failure, we need systemic change.

• Failure must be examined, not just experienced. Founders should not simply accept failure as a rite of passage; they should be taught how to analyze it. Structured post-mortems, founder retrospectives, and real-time reflection should become standard practice.
• Investor-founder relationships must be redefined. Startups should not approach investors with the mindset of please, sir, can I have some more? but rather as partners in a high-risk venture. Due diligence must go both ways.
• The industry must reward resilience, not just hype. We need to celebrate the founders who navigate failure with integrity, those who iterate intelligently, and those who demonstrate staying power, not just the ones who make headlines with massive funding rounds.

Failure is not a badge of shame, nor is it a shortcut to wisdom. It is a tool—one that must be wielded correctly. The final question is not whether failure will happen, but whether the startup world is finally willing to learn from it.

We'll be back next week with fresh scoops following incredible experiences (and the people who attend them).