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Crossroads: Deciding to Sell Your Business vs. Doubling Down

As a triumphant entrepreneur, your journey has been shaped by the harmonious interplay of ambition and practicality. Now, at this pivotal juncture, the question looms large: Forge ahead with unwavering resolve, or consider a strategic transition?

The specter of rivals potentially wresting control of your enterprise weighs heavily on your mind – a decisive blow that could spell irrevocable defeat. Yet, doubling down holds the promise of a grand triumph on the horizon. On the contrary, should you opt to part ways now, the lingering thought of untapped potential may haunt you.

This juncture demands a verdict that will cast a profound influence over the chapters that await you. Moments such as these often materialize in response to external forces, fleeting in nature. It’s vital to embark upon this decision thoughtfully and purposefully. Bear in mind, the truth navigates an uncharted realm, devoid of absolutes.

Sell Your Business vs. Doubling Down

So, what course of action should you undertake?

The answer is a tapestry woven from the threads of your individuality and the currents of your industry. Look both inward, delving into your essence, and outward, casting your gaze upon the dynamic landscape of your sector.

In the forthcoming discourse, we illuminate the pathway to this dual-faceted vision.

Look Outward – On the State of Your Industry

Strategic financial infusion is your vessel to maintain and advance your competitive edge. Rather than extracting funds from your enterprise, channeling resources back into it becomes the linchpin of your success—a counterintuitive strategy, particularly at this juncture of your journey.

You might find yourself at a juncture where wealth diversification seems alluring, an endeavor to spread your resources across varied avenues rather than a single reservoir. The perceived risk of housing a substantial chunk of your net worth within a solitary, illiquid vessel—your business—looms large. A hypothetical scenario emerges: a competitor’s onslaught threatens to engulf your enterprise, potentially eradicating a significant portion of your net worth.

Consequently, a pivotal choice stands before you—double down or divest. Failure to fortify your position could leave you vulnerable, trampled by rival forces, sealing your fate prematurely. Yet, perhaps you’ve already woven intricate blueprints, envisioning a captivating foray into the culinary landscape, such as launching a burger haven. The dichotomy emerges: part ways and secure your gains, or embrace the challenge and potentially spend a lifetime as a master of the griddle.

Objectively Evaluate Your Business

Gathering knowledge involves amassing information, while wisdom entails streamlining that information. Begin by accumulating knowledge, then take a step back to distill the gathered information.

Step 1: Collect Information

Gather the essential insights and facts about your business, industry, and competition:

Your Business

  • Determine the trajectory of your revenues: are they stabilizing, declining, or on the rise?
  • Evaluate your gross margins: are they holding steady, diminishing, or improving?
  • Assess the trend in your net profits: are they maintaining, decreasing, or growing?
  • Scrutinize your value proposition’s competitive edge.
  • Evaluate your competitive standing: are you gaining or losing ground?

The Industry

  • Examine the landscape: Is your industry marked by fragmentation and numerous small businesses, or is it gradually consolidating?
  • Ascertain the growth dynamics: Is your industry expanding, or is it encountering a downturn?

The Competition

  • Analyze market share dynamics: Are your competitors chipping away at your slice of the pie? Is your market share gradually eroding?
  • Assess competitor strength: Where do your rivals stand in terms of prowess?
  • Identify institutional-backed newcomers: Are any fresh contenders fueled by institutional resources like venture capital?
  • Monitor disruptive value propositions: Have competitors introduced game-changing propositions that could redefine the industry and potentially render your business outdated?
  • Strategize for competitive relevance: Determine whether incremental innovation suffices, or if bold transformations are imperative.

During the information-gathering phase, maintain an impartial perspective. Focus solely on gathering facts – embrace objectivity without the burden of immediate assessment. Once data is amassed, the ensuing steps involve astute analysis and synthesis.

Step 2: Simplify Information

Once you’ve meticulously gathered this data, harness the potency of wisdom to distill it. Maintain unwavering honesty when assessing your industry’s condition – refrain from allowing emotions to outmaneuver rationality. Streamline your findings into three core realms:

Your Business:

  • Is your business ascending while retaining its competitive edge, or do you find yourself navigating a gradual descent?
  • In instances of decline, introspect candidly. Does it stem from a skill deficiency or a waning drive? Alternatively, could your competition simply hold a stronger foothold? Should skill or motivation falter while competition thrives, it’s prudent to consider an exit.

However, should your business thrive and your value proposition stand unwavering, a sale may not be a requisite avenue.

The Industry:

  • Does your industry exhibit growth or languish in decline? Are rivals in the process of strategic consolidation?
  • Should your industry experience a decline, a proactive stance might involve a value proposition transformation, unless the option to forge a new path beckons.

The Competition:

  • Is the competitive landscape robust, wielding the potential to swiftly overshadow your presence?
  • Should your competitors prove robust, growing with unwavering momentum, and you recognize limitations in your ability or motivation to contend, a strategic sale becomes a consideration.

Through a confident lens, apply these distilled insights to map your strategic journey ahead.

Look Inward – On Yourself

Having scrutinized your business and industry, the moment has come to direct your gaze inward — towards yourself. While dissecting your business and industry engages your intellect, this inward reflection engages the core of your being.

Thoroughly consider each of the three following areas.

Step 1: Assess Your Skills

Assess your competitive prowess: Are you equipped with the requisite skills? If not, do you possess the determination to swiftly acquire them? Is the competition of such formidable strength that skill acquisition would fall short in the face of their dominance? This scenario often surfaces within innovative sectors demanding profound technical acumen, like software development.

When confronted with an expertise gap and the struggle to keep pace with competitors, two decisive paths beckon:

  • Forge Ahead: Redefine your presence in the industry by specializing or securing funding for enhanced competition readiness.
  • Embrace Transition: Opt to exit the race, with the strategic sale of your business as a prudent alternative.

Step 2: Assess Your Motivation

Are you fueled by the vigor and determination required for your business’s journey? In a fiercely competitive landscape where rivals nibble at your market share, an exceptional reservoir of motivation becomes your armor for sustained competitiveness. Conversely, in a realm of feeble competition, a standard measure of drive often suffices.

Do you find yourself drained? Probe the root. Is it a decade devoid of respite that has brought you to this point, or perhaps a profound discontent with your industry? While stagnant waters flow with the current, your vitality dictates an alternate course. Should burnout plague you and your industry’s contenders surge ever stronger, pragmatic introspection is warranted to gauge your capacity to counter the tide.

Step 3: Consider Your Dreams

Evaluate your passion for your business. Reflect: Is it a genuine, unwavering love? Given your current insights, would you embark on this journey anew? Project your aspirations onto the canvas of five, ten, or twenty years from today. Are you primed, both emotionally and financially, for a potential retirement?

The foundation for unraveling these answers rests upon self-awareness. What ignites your joy? What fuels your enthusiasm? Picture your ideal day—its contours and colors. Does your business interlace harmoniously with your aspirations, or does your heart whisper of different horizons? If an alternate resonance stirs within, perhaps it’s time for an elegant transition. Uncertain? Then your compass is simple: delve into the depths of self-understanding.

For many entrepreneurs, the whirlwind of busyness eclipses the quest for self-discovery. This pursuit demands precious time and unwavering exploration. Document your thoughts. Immerse in autobiographies. Engage fellow entrepreneurs. Venture into the world, for travel is not just a voyage of sightseeing but a pilgrimage to self-discovery. It kindles our potential, revealing the plausible. As Simone Weil aptly put, “Attachment is the great architect of illusions; reality is attained only by those who detach.” Travel, the elixir of detachment, unravels our illusions, granting clarity to perceive the veracity before us.

Signs You Should Double Down

Key Indicators for Strategic Reinforcement:

Your Business, Industry & Competitors

  • Your Business: A meticulous assembly of substantial industry data leads you to a pragmatic conclusion: your competitive stance is poised for endurance. Witnessing sustained growth, your unique strengths beckon, even amidst incremental innovations.
  • Industry: A sunlit trajectory graces your industry, casting a hopeful glow upon your venture. The absence of swift consolidation underscores the enduring triumph of independent operators.
  • Competition: The competitive landscape bears a favorable complexion. Impending overshadowing by rivals remains unlikely, and the advent of institutional-backed novices or game-changing propositions is absent from recent memory.

Financial Considerations

  • Net Worth: Your financial portfolio is thoughtfully diversified, liberating your retirement prospects from sole reliance on business sale.
  • Reinvestment: A monetary reservoir exists to fuel business reinvestment, if requisite for sustained competitiveness.

Personal Dynamics

  • Motivation: Innate ardor fuels your enterprise—propelling you forward with vigor and resilience.
  • Proficiency: Competence is your hallmark, adeptly steering you toward continued relevance.
  • Purposeful Alignment: The resonance of your business with your aspirations signifies an enduring alliance, fortified by devotion.

Signs You Should Sell

Indicators Pointing Toward Strategic Consideration:

Your Business, Industry & Competitors

Your Business:

Observing a decline in revenue and a gradual erosion of your value proposition, the viability of incremental innovation wanes. Absent a robust resurgence, the trajectory appears ominous, forewarning potential failure. Resolute action is requisite to navigate this crossroads.


  • Economic Landscape: Signs of industry decline loom, casting shadows on growth prospects.
  • Mergers & Acquisitions Landscape: An acquisition surge pervades your industry, as behemoths swiftly assimilate smaller entities to clinch dominance. While this may inflate valuations, it simultaneously amplifies competition.
  • A strategic juncture emerges wherein calculated decisions are imperative—selling could manifest as the prudent path. Notably, in domains characterized by fierce ‘winner takes all’ dynamics, a condensed window of opportunity necessitates swifter strategic maneuvers. If capital, expertise, or fervor for competition is lacking, opting to sell can prove astute.
  • Competition: Formidable adversaries populate your competitive sphere, necessitating perpetual engagement to avert impending obsolescence. Vigilance against nimble challengers, often unseen and unnoticed, is paramount to sustain relevance.

Financial Dynamics

  • Net Worth: A substantial share of your wealth is tethered to your enterprise—a scenario prompting introspection, especially if retirement security hinges solely on a business sale.
  • Reinvestment: The financial landscape constrains the ability to channel cash influx into business fortification, a potential vulnerability that necessitates evaluation.

Personal Considerations

  • Motivation & Alignment: The harmony between your business and personal aspirations bears significance. Should a chasm exist between your entrepreneurial engagement and your broader life ambitions, it warrants introspection.
  • Aptitude: Competence proves pivotal for competitive endurance. If this attribute is lacking, recalibration merits contemplation.
  • Vitality & Burnout: Exhaustion’s grip on motivation and vitality raises concern, rendering competitiveness an uphill pursuit.
  • Alignment with Dreams: An incongruence between personal dreams and business realities underscores the need for deliberate appraisal.

On Being Flexible

Embrace the Decision to Redouble Efforts:

As you opt to intensify your commitment to your enterprise, vigilance over your industry becomes paramount. Adaptability and flexibility are your allies, poised to navigate shifts in both your sector and the broader market landscape. Anticipate the potential recalibration of your timeline, molded by market ebbs and flows, defying rigid confines.

Imagine a scenario: you target a $10 million revenue milestone as the trigger for a sale, but sudden acquisition fervor propels multiples skyward—promptly necessitating a readiness to act.

Embarking on a sale journey unfolds within a timeframe that fluctuates, spanning from three to twelve months, with potential extensions. The transition phase often necessitates your stewardship for a subsequent one to two years—a commitment intrinsic to industry norms. Your blueprint for departure might require initiation several years in advance, aligning with the unique cadence of your domain.

Stay attuned to the dynamics of change, whether gleaned from newfound industry insights or revelations about yourself. In the chronicles of time, truth unfurls its layers, gradually unveiling itself in unexpected junctures.

Exploring Alternatives to a Sale

Exploring Strategic Alternatives Beyond Direct Sale:


Stepping onto the landscape of strategic alternatives, recapitalization emerges as a compelling avenue. In this scenario, a partial divestment of your company unfolds, often to the stewardship of a private equity (PE) group or corporate venture fund. Consider this: a stake of 20%, 40%, or 60% may shift hands, accentuating the spectrum from minority to majority interest. A pivotal facet rests on your ongoing operational role within the entity.

A recapitalization presents a unique juncture to harvest immediate gains while preserving a strategic stake. This dual-layered approach not only crystallizes gains, fostering financial diversity, but also primes the stage for a potential encore exit. A future panorama unfurls—a subsequent sale of the remaining 70% to a distinct buyer, be it a publicly traded entity or a strategic industry counterpart.

Delving into this dynamic, private equity groups and corporate venture entities engage with an explicit aim: to invest in promising enterprises, rich with latent potential. The trajectory envisages a value ascent, materializing either through eventual divestment with significant gains (typically in three to seven years, for PE firms), or integration within the fold of a corporate venture enterprise.

For you, a realm of benefits beckons. Unlocking the present, you secure a portion of your gains, then pivot to a collaborative chapter within the larger ecosystem—a trajectory that can culminate in retirement or the inception of your next visionary pursuit. Augmenting this voyage, the acquiring entity ushers in enhanced capabilities and resources, accentuating your potential through broader distribution channels and the amplification of an established brand.

Intrinsically suited if you:

  • Steer a venture fortified by robust competitive advantage, poised for industry-opportunity exploitation via third-party expertise or capital infusion.
  • Commit to a post-closing tenure of one to three years or potentially longer.
  • Aspire to infuse your wealth portfolio with diversity, orchestrating an adept ‘take chips off the table’ maneuver.

Raising Money

Elevating Capital: Unveiling Equity’s Potential

Venturing into capital acquisition, equity emerges as a formidable avenue, distinct from the realm of debt. Our focus centers on the sale of equity, a dynamic poised to unfold predominantly through venture capitalists (VCs). This avenue, tailored to the audacious arena of high-growth prospects, beckons with the allure of investor returns ranging from 10 to 100 percent.

In parallel with a recapitalization, this voyage entails relinquishing a portion of your enterprise—converting it into equity for external investment. Yet, discerning characteristics set this course apart, guided by distinct benchmarks that befit this venture.

Securing funding from VCs orchestrates a rigorous journey that may span a year, marked by meticulous scrutiny. The cost of capital, in this case, often demands a relinquishment of some level of operational control. VCs converge upon ultra high-growth prospects, envisioned as potential juggernauts, poised to ascend into the echelons of nine-figure enterprises ($100 million and beyond). It’s worth noting that the VC path is one paved with rigor and uncertainty; fewer than 3% of aspirants traverse this transformative junction, and a notable share of VC-backed initiatives culminate in unmet expectations.


The Defining Dilemma: Selling or Doubling Down?

In the journey of every entrepreneur, a pivotal crossroads emerges: the choice between selling or doubling down. This decision’s reverberations extend to shape your life’s course. Entrepreneurship, with its weighty challenges and exhilarating prospects, stands as a high-stakes pursuit. Navigate this juncture by probing both within, towards self-discovery, and outward, towards your industry’s landscape. Through thorough introspection and diligent industry analysis, you often unearth that the decision itself has crystallized.

“Nothing in this life is to be feared. It is only to be understood.” – Marie Curie

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