Entrepreneurship through acquisition in the digital age: exploring website ownership patterns and motivations for selling

Entrepreneurship attracts many, but for most, it remains an unfulfilled dream. The fear of failure, lack of resources and the inherent difficulties of starting a business often impede aspiring entrepreneurs from realizing their vision (Henriquez-Daza et al., 2024). Those who attempt to start their own businesses are often confronted with a harsh reality where the odds are stacked against them, and many fail due to challenges such as inadequate product-market fit, credibility issues and financial constraints (Feinleib, 2011; Holtz-Eakin et al., 1994; Townsend et al., 2010). Against this backdrop, entrepreneurship through acquisition (ETA) has emerged as a promising alternative to the traditional entrepreneurial path, allowing aspiring entrepreneurs to bypass many of the initial hurdles by acquiring an established business with a proven track record (Kelly and Heston, 2024).

ETA’s relevance extends beyond the realm of individual entrepreneurial aspiration. As industrialized nations confront a looming succession crisis, with a significant number of business owners approaching retirement without clear transition plans, the need for effective succession strategies has never been more pressing (Pahnke et al., 2024; Reester, 2008; Umans et al., 2024). In Germany alone, over 620,000 SMEs are projected to face succession challenges by 2027 (Schwartz, 2024), whereas over 2m small businesses are owned by Baby Boomers in the USA, who are nearing retirement age with many lacking succession plans (Nows, 2021). This crisis represents a threat to the livelihoods of employees, the legacies of retiring entrepreneurs and the economic stability of communities and nations. Moreover, succession planning is not limited to retirement as entrepreneurs might seek to exit their businesses for various reasons, including new strategic opportunities, shifting personal goals or financial considerations. Research shows that many entrepreneurs leave their ventures earlier than expected, not necessarily due to failure but owing to changing circumstances (Ronstadt, 1986). ETA offers a practical solution to these challenges, providing a path for aspiring entrepreneurs to take the reins of established businesses and carry them into the future.

While ETA has gained traction in traditional brick-and-mortar businesses, its potential in the digital realm—particularly in web-based SMEs—remains largely untapped (Hoffmann et al., 2023a). While digital businesses have demonstrated resilience and significant growth potential in the digital era (Allen, 2019; Sahut et al., 2021), the entrepreneurs behind them, their business models and the effects on the entrepreneurial process remain notably underexplored within academic research (Elia et al., 2020; Sally et al., 2015; Sussan and Acs, 2017). This study aims to bridge this gap by exploring the untapped potential of web-based SME acquisition as a strategic move for aspiring and established entrepreneurs. We explore the motivations, characteristics and selling propensities of these digital entrepreneurs through a qualitative approach involving in-depth interviews with 19 owners of established websites, assessing the viability of their enterprises as promising assets for acquisition in the context of ETA.

We aim to equip entrepreneurs with the knowledge and tools they need to succeed in acquiring web-based businesses by shedding light on the associated opportunities and challenges. The significance of this work lies not only in its potential to unlock new pathways for entrepreneurship but also in its capacity to address the pressing succession crisis. By facilitating the handover of digital businesses to new owners, ETA can help preserve jobs, maintain the vitality of online communities and contribute to overall economic resilience in the face of demographic shifts. We aim to fundamentally advance scholars’ understanding of ETA in the digital realm and equip entrepreneurs with the necessary knowledge and tools to succeed in this rapidly evolving space.

The historical roots of ETA can be traced back to the development of the modern buy-out market in the 1970s (Castellaneta et al., 2018). This decade marked a shift in corporate acquisition strategies, characterized by the transfer of large corporations—including listed and family firms—to private entities. These transfers were predominantly financed through substantial debt leveraging, complemented by smaller equity contributions from specialist investors. The scale of transactions dramatically expanded as the buy-out market evolved in the 1980s, and billion-dollar buy-outs began to overshadow the smaller-scale deals of the previous decade (Lowenstein, 1986). However, the nuances within the buy-out market—particularly those pertaining to smaller, non-private-equity-funded company takeovers—have remained underexplored in academic research, leading to ETA being conflated with larger-scale, leveraged buy-outs (Hunt and Fund, 2012).

The late 1980s saw a paradigm shift with the introduction of the term “entrepreneurial leveraged buy-out,” which recognized the unique nature of leveraged buy-outs of small companies driven by entrepreneurial motives rather than financial engineering (Cooper and Dunkelberg, 1986; Malone, 1989). This distinction set the stage for a more nuanced understanding of ETA, recognizing its role as a distinct form of entrepreneurship within the corporate acquisition landscape.

The relevance of ETA has surged in recent years, both among practitioners and in academic circles (Hoffmann et al., 2023a). This growing interest is partly driven by the increasing number of companies facing succession challenges as a generation of entrepreneurs and business owners approach retirement (Nows, 2021). The ETA trend is not limited to a specific sector or region but rather is a global phenomenon offering a sustainable model for business continuity and growth (Kaplan and Stromberg, 2009; Kolarova et al., 2020).

The digital transformation of business has fundamentally altered the landscape of entrepreneurial opportunities. As academic interest in ETA grows, research has primarily focused on traditional business models, with limited attention devoted to web-based SMEs (Sally et al., 2015). While academic interest has begun to parallel the practical shift by dedicating more resources to understanding and exploring the intricacies of ETA, a significant gap remains in the literature concerning the specific context of web-based SMEs.

Acquiring web-based SMEs presents distinct opportunities and challenges that set them apart from traditional business transfers. Assessing the value and potential of these businesses, navigating the technical and operational complexities of digital operations and understanding the motivations and strategies of digital entrepreneurs are all crucial areas for further exploration. In exploring these challenges, this paper aims to contribute to the growing body of knowledge on ETA and provide valuable insights for those considering this path to entrepreneurship in the digital age.

Given the early state of research on ETA, particularly in the context of web-based SMEs and their impact on enterprising communities, this study employs a qualitative approach, which is particularly valuable for investigating novel or underexplored topics (Gioia and Pitre, 1990; Marschan-Piekkari and Welch, 2004; Maxwell, 2012). This methodology enables an in-depth exploration of website owners’ experiences, strategies and motivations in running and potentially selling their online businesses.

In this study, data was gathered through expert interviews with 19 digital entrepreneurs who had created or managed online businesses (i.e. websites). The interviewees were selected using purposive sampling to ensure their diverse backgrounds, industries and geographical locations. The participants came from various countries, including the USA, Germany, Canada, Australia and India, and operated in various niches, such as finance, travel, nutrition and psychology. This geographical and industry diversity allowed us to explore how different contexts influence entrepreneurs’ perspectives on website ownership and exit strategies. The gender distribution of the interviewees was balanced, with both male and female website owners represented. The interviewees’ websites ranged in age from 1.5 to 17 years, reflecting a mix of newer and more established online businesses. The primary monetization methods that the websites used included advertising, affiliate marketing, sponsored content, digital products and e-commerce sales. The sample size of 19 participants was determined based on the data saturation principle (Guest et al., 2006), which was reached when no new themes or insights emerged from the interviews.

The interviews were conducted using a semistructured format, covering key topics such as the website owners’ backgrounds, their motivations for starting and managing their websites, the unique features and value propositions of their online businesses, their strategies for managing and monetizing their sites and their thoughts on potentially selling their websites in the future. The interviews lasted approximately 25–45 min and were conducted via video conferencing or telephone, depending on the interviewee’s preference and availability. All interviews were audio-recorded and subsequently transcribed verbatim to facilitate a thorough analysis.

The data analysis followed the principles of Mayring’s (2010) methodological framework. The transcripts were systematically organized and coded using a specialized qualitative data analysis tool. An inductive coding approach was used to iteratively identify recurring themes and exemplary practices in digital entrepreneurship. These themes were determined based on their frequency and significance across the interviews, focusing on website management and monetization strategies, future expansion or diversification plans, the impact of emerging technologies such as artificial intelligence (AI) on digital businesses and the decision-making processes behind selling online businesses. The coding process involved multiple iterations to ensure consistency and comprehensiveness in identifying themes.

Our research into established website owners revealed valuable insights into digital entrepreneurship’s motivations, strategies and challenges, with significant implications for ETA in the digital context. The findings offer new perspectives on potential acquisition targets for ETA practitioners by illuminating key aspects of website ownership and management across diverse niches and industries. Our analysis provides a comprehensive picture of the current landscape of website entrepreneurship, with important considerations for both digital business practitioners and potential acquirers evaluating online assets.

The emergent themes encompass the characteristics and motivations of website entrepreneurs, the nature and value of digital assets, factors influencing the desire to sell websites and the transformative impact of AI on digital operations. Our findings underscore how web-based businesses differ from traditional enterprises while revealing the complex interplay of personal passion, financial objectives and technological disruption that shapes their acquisition potential. The following sections explore each theme in detail, providing actionable insights for digital ETA.

The study sample comprised a diverse group of website entrepreneurs from various geographical regions, including North America, Europe, Asia and Australia. This global representation underscores the borderless nature of website ownership and the potential for individuals from different cultural backgrounds to succeed in the digital marketplace. Gender diversity was also evident, suggesting equal opportunities for success in digital entrepreneurship.

The interviews revealed that website owners come from various professional backgrounds, such as journalism, education, biology and software engineering, bringing a wealth of skills and experiences to their digital ventures. Many reported starting their websites as side projects or hobbies, driven by a passion for their chosen niche or a desire to share their knowledge. These passion projects often evolved organically into thriving businesses, showcasing the transformative potential of website ownership.

The entrepreneurial spirit was a defining characteristic of these website owners as they displayed proactive business management qualities, often juggling multiple websites or online ventures. They were deeply involved in various aspects of their business, such as content creation, search engine optimization (SEO) and monetization strategies. This demonstrates a hands-on approach to digital entrepreneurship, exemplified by their willingness to learn and master new skills, such as coding, which enabled them to troubleshoot technical issues efficiently and reduce dependence on external developers.

Income levels significantly varied, with some treating their websites as supplementary income sources and others relying on them as primary financial support. Several owners of larger websites reported substantial six- to seven-figure annual revenues, highlighting the potential for financial success. This variation in income levels underscores the flexibility of website entrepreneurship in catering to different financial goals and lifestyles.

Continuous learning and skill development proved critical in website entrepreneurship. Many owners reported acquiring new skills as their websites evolved, such as SEO, content creation, Web development and digital marketing. This willingness to adapt was seen as essential for maintaining competitiveness in the evolving digital landscape. Participants emphasized the importance of keeping up with industry trends and best practices to sustain their websites’ growth and success.

Three key motivations emerged for website ownership: financial objectives, the pursuit of freedom and autonomy and personal passion or interest. Financial goals ranged from generating supplemental income to achieving financial independence. The pursuit of freedom and autonomy was a critical motivator, with entrepreneurs seeking greater control over their work-life balance and the opportunity to engage in creative and entrepreneurial activities. Personal passion often influenced niche selection, ensuring sustained commitment to projects and fostering the entrepreneurs’ deep connection with their digital ventures.

Diversification and risk mitigation strategies were also prominent themes in the interviews. Many website owners expressed a desire to manage multiple projects simultaneously to mitigate the impact of market volatility, search engine algorithm updates, or shifts in monetization strategies. This diversification mindset reflects the dynamic nature of the digital landscape and the need for adaptability in the face of constant change.

Understanding these diverse backgrounds, skill sets and motivations is crucial for potential acquirers in the ETA context, enabling them to grasp the nuances behind why website owners start, grow and might ultimately be willing to sell their online businesses. By appreciating the diverse factors that drive website creators, potential acquirers can tailor their acquisition strategies, making them more appealing to sellers who see their websites as more than simply businesses but rather embodiments of their aspirations and efforts. Recognizing these website owners’ passion, skills and resilience can help acquirers navigate the acquisition process more effectively and unlock the full potential of the digital assets acquired.

The websites exhibited notable patterns in audience reach, monetization methods and operational complexity. Many targeted specific niches, resulting in a focused and engaged user base. This strategic targeting fosters a dedicated community of users and provides a competitive advantage. By concentrating on niche markets, website owners can carve out a unique space in the online world, offering tailored content, products, or services to a specific audience.

Operating within less crowded niches makes it easier for websites to succeed at SEO and establish authority, with fewer legacy brands dominating these spaces. The internet’s global reach turns even narrow niches often overlooked by larger companies into sizable markets, offering unique growth opportunities. Moreover, the ability to expand reach, diversify content and explore new monetization opportunities highlights web-based businesses’ scalability and growth potential, making them attractive assets for acquisition.

Despite most being English-language websites, owners consciously focused on specific geographic regions. This strategic decision was influenced by the understanding that monetization opportunities—such as ad placements—can significantly differ based on regional factors. Given that the revenue generated per thousand ad impressions (RPM) can strongly vary depending on the geographic location of the website’s audience, some sites primarily targeted US-based audiences to capitalize on higher monetization potential, whereas those in very small niches often pursued an international audience to ensure profitability.

Monetization strategies varied, with affiliate marketing emerging as a common revenue stream. Its success largely depended on the website’s niche and audience engagement, with some owners reporting significant income from well-chosen affiliate partnerships. Google AdSense and ad networks such as Mediavine and AdThrive were also widely used for ad publishing, with several interviewees mentioning these platforms as their primary income sources. The choice of ad network often depended on traffic volume, with some owners transitioning to more premium networks as their sites grew. Some owners forged direct partnerships with larger brands, leading to significant revenue opportunities through sponsored content or long-term collaborations. In addition, several website owners diversified their income streams by creating and selling digital products such as online courses, e-books and printables, boosting revenue and enhancing their authority within their niche. A few entrepreneurs also explored membership models or premium content offerings, although these strategies’ success varied depending on the website’s audience and subject matter.

Audience engagement and community building emerged as critical assets for the websites. Many owners emphasized the importance of fostering strong connections with their users through personal anecdotes, helpful information and responsive communication, enhancing user loyalty and contributing to the website’s overall value. A dedicated and active community can provide valuable feedback, help spread the website’s content through word-of-mouth and even contribute user-generated content, further strengthening the website’s authority and appeal.

Another notable insight was the role of personal branding and authenticity in creating value for websites. Several website owners highlighted the importance of injecting their unique personality and voice into their content, which resonates with their target audience and sets them apart from competitors. This personal touch often goes hand-in-hand with audience engagement efforts, creating a synergistic effect. A strong personal brand can be valuable in establishing trust and credibility with the audience, making the website more appealing to potential buyers who recognize the value of a loyal and engaged community. However, this close association between the website and the owner’s personal brand can also present challenges when considering selling the website, as the new ownership transition might require careful planning to maintain the audience connection.

Operational complexity varied among the websites, reflecting diverse owner strategies and resource allocation. While some managed their sites independently, larger websites often used teams for content creation, technical support and marketing. A trend toward hiring international employees and freelancers was observed, driven by lower wage rates and workforce scalability benefits. Several owners mentioned utilizing virtual assistants—particularly from countries including the Philippines—for repetitive tasks and backend operations. Some entrepreneurs strategically built networks of freelancers with specialized skills such as Web development, often sourcing talent from Eastern European countries.

A complex interplay of emotional, financial and strategic factors unique to each website owner influences the decision to sell their business. Website owners often developed a strong emotional attachment to their digital ventures, viewing them as their “baby” or an extension of themselves. This deep connection can make selling emotionally challenging, as the website represents a significant part of their life and experience. As the content of the websites is often a reflection of personal viewpoints and experiences, it can make the thought of selling not only a business decision but a profoundly personal one.

However, financial considerations also play a crucial role in the decision-making process. Some website owners prioritized the ongoing income generated by their websites over a lump sum payout, particularly if the website provided a steady and reliable income stream. They assessed the potential earnings from a sale against the long-term financial benefits of continuing to operate the website themselves. For others, the prospect of a significant lump sum payout was considered an attractive option, especially if it could provide long-term financial security, fund other projects or be reinvested into diverse passive income opportunities.

Finding a buyer who aligns with their values and vision is crucial for those open to selling. Website owners often emphasized the importance of finding a buyer who would maintain the integrity and vision of the website, ensuring that the audience would continue to receive value. They were seeking buyers who shared their passion and expertise and would take care of the community that they built. The buyer’s alignment with the website’s mission and values emerged as a key consideration in the decision to sell.

Concerns about the website’s future under new ownership also influenced the desire to sell. Some website owners worried that selling might lead to the website’s decline or failure if the new owner lacked the same level of passion, expertise and commitment. They feared that the website’s unique voice and value proposition might be lost in the transition, potentially alienating the audience that they had worked hard to cultivate.

Personal circumstances and life changes also influenced the decision to sell. Factors such as retirement, health issues or a desire to pursue other projects were mentioned as potential reasons for considering a sale. In such cases, selling the website was seen as an opportunity to move on to a new chapter in life while ensuring that the website continues to thrive under new ownership.

Website owners’ perceptions of the market and the potential valuation of their websites varied. Some felt that their websites were undervalued or that potential buyers did not fully appreciate the unique aspects of their business, which made them hesitant to consider selling. Others were more optimistic about the market and believed that there would be interested buyers if they decided to sell, particularly if the website was performing well and had a strong track record of success.

Traffic fluctuations and the impact of search engine algorithm updates also strongly influenced the desire to sell. Website owners understood that the decline in traffic resulting from these updates could significantly devalue their site. This uncertainty can prompt considerations of selling, although this decision is weighed against the site’s history, recovery potential and the owner’s emotional investment. Some website owners mentioned that they would consider selling if the timing was right or if market conditions were favorable, emphasizing the importance of selling at a peak or when the website was performing well to maximize its value.

A website’s complexity and personal elements further influence the desire to sell. Sites with multiple components—such as podcasts or newsletters—can be challenging to maintain as a passive asset, potentially dissuading buyers seeking more straightforward investments. The presence of personal elements such as family photos or personal stories can also increase an owner’s reluctance to sell, as the website has become a tapestry of their life and experience.

However, not all website owners were interested in selling. A few expressed a lack of confidence in finding a suitable buyer or simply had no desire to part with their website, viewing it as an integral part of their identity and purpose. Some owners emphasized that their websites represented years of accumulated knowledge and expertise in their niche, making it challenging to imagine transferring this to a new owner. Others highlighted the unique value proposition of their content, noting that their personal experiences and insights were irreplaceable assets that AI or generic content could not replicate. In addition, some website owners saw their digital ventures as ongoing projects with untapped potential, preferring to continue developing and scaling their sites rather than selling. Many found the idea of walking away from a business they had built from the ground up unappealing, especially when they felt that there remained room for growth and improvement.

The decision to sell a website is multifaceted, with financial considerations deeply intertwined with personal sentiments and each website’s unique journey. Potential buyers should approach the acquisition of web-based businesses with empathy and a meticulous assessment strategy, recognizing that these sites are often more than simply financial assets. Adopting a targeted and careful outreach approach acknowledging the website’s unique intricacies and inherent personal connections can ensure a more respectful and effective negotiation process, particularly for websites with a strong personal imprint from their owners.

The impact of AI on website operations elicited a wide spectrum of responses from owners, reflecting the dynamic interplay between technology and content creation. AI was often viewed as a double-edged sword, with website owners recognizing its potential to streamline content production and scale their online presence while also expressing concerns about the authenticity and quality of AI-generated content. For prospective buyers, these diverse AI adoption strategies offer insights into immediate operational efficiencies and long-term growth potential, particularly in markets where content authenticity drives audience engagement.

Many website owners acknowledged the utility of AI in ramping up content production, seeing it as a tool to expand their online presence more efficiently. They appreciated its ability to quickly generate content outlines, introductions, or even entire drafts, which can be particularly beneficial for websites that strongly rely on a steady stream of new material to attract and engage audiences. However, they emphasized the importance of human oversight and editing to ensure the quality and accuracy of the AI-generated content.

A notable division existed within the community regarding their sentiments toward AI, with some owners voicing apprehensions about potential traffic losses and being overshadowed by AI-generated content. They worried that an over-reliance on AI might dilute the uniqueness and personal touch that sets their websites apart, potentially eroding audience trust and engagement.

Some website owners staunchly advocated for the value of human-curated content, emphasizing its authenticity and irreplaceable nature. They believe that AI cannot replicate the personal experiences, anecdotes and expertise shared through their content, while highlighting that this human element is what most strongly resonates with their audience. While AI can generate generic content or basic information, it often falls short when providing in-depth expertise, nuanced perspectives, or the personal touch that engages users. The lack of personal experience and industry-specific knowledge can result in content lacking the depth and relevance of human-created content.

Interestingly, the trajectory of AI adoption varied among website owners. Some had experienced initial apprehension, particularly concerning the detection of AI-generated content by search engines and its potential impact on search rankings. However, as AI becomes more sophisticated and integrated into content creation processes, there has been a gradual shift toward a more accepting attitude. Website owners increasingly view AI as a tool to use with human oversight and editing to balance efficiency and quality.

The risk of content duplication or misuse of AI-generated material was another concern expressed by website owners. They worried about the potential for larger entities with significant domain authority to exploit AI to produce content that might overshadow or even plagiarize their own. This underscores the importance of maintaining a strong brand identity and fostering a personal connection with the audience, reflecting aspects that AI still struggles to replicate effectively.

Amidst these concerns, a pragmatic approach emerged, whereby website owners viewed AI as a complementary tool in the content creation process rather than a complete replacement for human creativity and insight. By leveraging AI to streamline tasks such as research or content outlining, these owners seek to harness AI’s benefits while retaining the critical role of human oversight and personalization to mitigate its potential drawbacks.

For potential website buyers, the increasing adoption of AI in content creation presents both opportunities and challenges. While AI can be a valuable tool to scale content production and maintain a consistent publishing schedule post-acquisition, buyers must also be aware of the potential pitfalls of an over-reliance on AI, such as the risk of producing generic or inauthentic content that fails to resonate with the website’s audience. When evaluating a website for acquisition, buyers should assess the extent to which AI is used and how it is integrated into the content creation process. They should also consider the website’s brand identity, audience engagement and the role of human-created content in maintaining the site’s unique value proposition. Striking an appropriate balance between leveraging the efficiency of AI and preserving the human touch is crucial for buyers seeking to maintain and grow the value of their websites acquired in the era of AI-driven content creation.

In conclusion, website owners’ perspectives on AI form a wide spectrum, from optimism about its potential to streamline content creation to concerns about maintaining their content’s authenticity and competitive edge. While acknowledging the capabilities of AI, there is a prevailing awareness of its limitations and the irreplaceable value of human creativity and expertise. As AI further develops, website owners must navigate this changing landscape, leveraging the technology to their advantage while preserving the unique voice and value proposition that sets their websites apart.

A promising shift has become increasingly apparent in our exploration of the concept of ETA as an underutilized pathway in the quest for business ownership. In the realm of ETA, there is a growing need to recognize the potential of digital assets—particularly web-based SMEs—as viable and valuable targets for acquisition (Hunt and Fund, 2012; Kreiterling, 2023). This realization marks a crucial expansion to the scope of ETA, urging aspiring entrepreneurs to consider these digital ventures not only as optional but rather as integral components of their entrepreneurial journey.

In the context of ETA, the compelling nature of digital assets lies in their distinct advantages over traditional physical businesses. These digital platforms often require less initial capital, are inherently scalable, and provide immediate access to a global audience (Ruggieri et al., 2019). Their operational flexibility, diverse revenue generation models and ability to rapidly adapt to changing market trends make them standout candidates for acquisition.

This section underscores the importance of embracing digital assets in ETA, as promising and strategic investments for those venturing into business ownership. Entrepreneurs can unlock new avenues for growth and success in the modern business environment by acknowledging the unique opportunities and navigating the inherent challenges in online entrepreneurship.

Insights from website owner interviews highlight the characteristics that make digital assets attractive for acquisition. Table 1 compares traditional and website businesses, illustrating why digital ventures are compelling ETA targets.

While standard due diligence remains crucial, several factors demand particular attention when evaluating web-based SMEs. Key considerations include business model viability, revenue generation mechanisms, market position and growth potential, all of which are particularly volatile in the digital space. Buyers should be vigilant for red flags such as declining traffic, poor revenue diversification or scalability issues.

The evaluation should extend beyond assessing a business’s current state and future potential. Understanding a seller’s motivations plays an essential role in the acquisition process. These motivations can range from financial needs to personal life changes to a shift in business focus. Understanding why an owner is selling can provide invaluable clues about the business’s health and potential. For example, a sale driven by financial difficulties might suggest inherent challenges within a business, whereas a sale for personal reasons (e.g. retirement) could indicate a well-functioning entity. Knowing the reason for a sale is critical for assessing an asset’s value and shaping negotiation strategies, allowing buyers to tailor their offers to the seller’s goals and expectations (Krukowski et al., 2023).

Operational complexity and niche targeting are also essential factors in evaluating a digital business. Operational aspects, including the technicalities of website management—such as SEO, content management and digital marketing—can significantly vary across different assets. Buyers must assess their ability to handle these elements, the feasibility of acquiring the necessary skills, or the potential to hire individuals with the required expertise. Niche targeting is a prevalent digital asset strategy whereby buyers should evaluate their understanding and capacity to engage with the specific market niche to which the website caters. This might necessitate a deep dive into the target audience’s preferences, the competitive landscape of the niche and the scalability of the website’s operational model.

The dynamics of the digital marketplace and the valuation of online assets are another critical area of consideration. The digital landscape is characterized by fluidity and rapid evolution, requiring buyers to have a firm grasp of current trends, competitor analysis and market saturation. In this context, valuation might diverge from traditional methods, focusing on industry-specific metrics such as traffic, engagement, recurring revenue, or monetization potential. In addition, external factors such as digital marketing regulations, search engine algorithm updates and the growing influence of AI on content creation can significantly influence a website’s future performance and value, making a thorough market analysis indispensable.

Buyers should also pay close attention to a website’s brand identity, audience engagement and the role of human-created content in maintaining the site’s unique value proposition. A strong brand identity and a loyal, engaged audience are valuable assets that can help mitigate the risks associated with algorithm updates and market fluctuations. The personal touch and in-depth expertise related to human-created content remain critical in building and sustaining audience trust and loyalty.

In summary, buyers in the digital ETA space must adopt a comprehensive and discerning approach to their acquisition plans. A thorough understanding of a seller’s motivations, a solid grasp of market dynamics, digital-business-specific valuation techniques, an awareness of the operational intricacies and niche focus of the digital asset, and a strategic approach to maintaining the website’s brand identity and audience engagement are all crucial elements that shape a well-informed, strategic acquisition decision. Adhering to this meticulous approach enhances the probability of a successful purchase and lays the groundwork for future growth and profitability of the acquired asset in an increasingly competitive digital landscape.

The trajectory of technological advancement—particularly in the context of AI—is reshaping the landscape of digital asset management and influencing the future outlook of ETA (Calderon-Monge and Ribeiro-Soriano, 2024). The progression of AI presents opportunities to enhance efficiency and scale content production while simultaneously introducing challenges related to content authenticity and potential duplication. Recent research shows that digital businesses face significant challenges in balancing data-driven operations with creative execution, suggesting that potential acquirers should evaluate a target’s analytical capabilities and creative assets to fully understand its potential (Hoffmann et al., 2023b). Understanding and adapting to these technological shifts is crucial for prospective buyers in the digital space.

Integrating AI in content creation has opened doors to unprecedented efficiency and scalability (Yadav et al., 2023). As noted earlier, AI tools can generate content at a pace and volume far surpassing human capabilities, enabling website owners to rapidly expand their online presence. This capability is particularly beneficial for websites that strongly rely on content production to attract traffic and engage audiences. However, this advantage is also associated with challenges as the ease of AI content generation raises concerns about the authenticity and uniqueness of the content. In a digital ecosystem where originality is a key driver of traffic and engagement, the potential for widespread content duplication can diminish the value of AI-generated material.

The development of AI is further poised to significantly affect search engine algorithms. As AI becomes more sophisticated in understanding and mimicking user behavior, search engines are likely to evolve in response, potentially altering the dynamics of online discoverability (Yu et al., 2023). This evolution will likely require new SEO and content marketing strategies as traditional approaches might become less effective. Keeping abreast of these changes and adapting acquisition and management strategies accordingly will be vital if buyers wish to maintain and grow their digital assets.

The ongoing evolution of search engine algorithms and the increasing emphasis on factors such as topical authority and user engagement pose both challenges and opportunities for website owners and potential acquirers. Buyers should prioritize websites with strong topical authority, a loyal user base and a track record of providing high-quality, user-centric content.

Another technological shift with far-reaching implications is the deprecation of third-party cookies, which significantly changes online advertising and monetization strategies (Alcobendas et al., 2023). Reduced reliance on third-party cookies and increased emphasis on privacy-focused browsing are challenging the efficacy of targeted advertising as a cornerstone of online revenue generation. This shift necessitates re-evaluating monetization strategies, particularly for websites that strongly rely on advertising revenues.

Technological advancements strongly influence the outlook of digital assets in ETA, particularly AI, and changes in online privacy norms. Prospective buyers must not only consider the current state of these assets but also anticipate and prepare for technological evolutions that will continue to shape the digital landscape. Adapting to these changes through content creation, SEO strategies, or monetization methods will be pivotal for the sustained success and growth of acquired digital properties.

In ETA, buyers considering website acquisitions face a landscape rife with potential risks. It is crucial to comprehensively understand these risks and possess effective mitigation strategies to transform these risks into manageable challenges, ensuring that websites remain an attractive—albeit often overlooked—asset class.

Given that market volatility in the digital arena—driven by shifts in consumer behavior, technology and competition—can significantly affect website traffic, revenue and relevance, buyers should seek websites with diverse traffic sources and revenue streams. Investing in multiple marketing channels and fostering a strong brand presence can enhance stability. In addition, building a portfolio of websites across different niches can further distribute risk.

Competition in the digital space is intense and constantly evolving. New competitors within a niche can swiftly emerge, and existing players can rapidly upscale or change direction (Brousseau and Pénard, 2008). Buyers should focus on websites in niche markets that present barriers to entry or require specialized knowledge. Assessing existing content quality, SEO strategies and user engagement levels can ensure a competitive advantage post-acquisition.

Regulatory changes—particularly concerning data privacy laws or advertising standards—can significantly affect online business operations (Alcobendas et al., 2023). Buyers should investigate the target website’s compliance with current regulations and assess the potential impact of upcoming changes. Legal consultation can be invaluable in navigating complex regulatory environments and adapting business models to meet these challenges.

The technological landscape presents challenges, especially in the context of AI’s evolving role and shifts in online privacy norms. Technological advancements should be embraced and incorporated into the business strategy. Maintaining agility and an openness to adopting new technologies can help businesses to remain relevant and competitive, although it is equally important to strike a balance between leveraging AI for efficiency and maintaining the human touch that resonates with audiences.

Given the rise of AI-generated content, concerns about content authenticity and the risk of duplication are increasingly prevalent. Investing in original, high-quality content creation and maintaining a unique brand identity can help to differentiate a website from competitors that rely on AI-generated material. Regularly auditing content and implementing strict quality control measures can help to mitigate the risks associated with AI-generated content.

Shifts in online advertising models such as deprecating third-party cookies present significant challenges to website revenue generation. Buyers should assess the reliance on traditional ad models and investigate existing efforts toward diversifying revenue streams. In addition, buyers should consider the potential for further monetization opportunities, ensuring the asset has sufficient flexibility to adapt to changing market conditions and maximize revenue stability.

Operational risks such as losing key personnel or technical failures can disrupt business continuity and influence a website’s performance. These risks are particularly acute for digital businesses, where downtime or data loss can lead to immediate revenue declines and long-term reputational damage. Implementing robust contingency plans, documenting essential processes (e.g. standard operating procedures) and investing in reliable infrastructure can help to minimize the impact of such risks. For instance, many website owners emphasize the importance of regular backups, using content delivery networks to mitigate server failures and employing redundant systems to ensure continuous operation.

By strategically addressing these risks, buyers can protect their investments while capitalizing on digital assets’ scalability and global reach. With careful risk assessment and solid mitigation planning, website acquisition can entice entrepreneurs who are eager to venture into or expand within the digital marketplace.

Our study of web-based SMEs reveals several critical avenues for future research, particularly regarding the digital entrepreneurial ecosystem and its community impact. While our study provides valuable insights, it is important to acknowledge certain limitations. Although our sample of 19 website owners achieved data saturation and represented diverse geographies, industries and experience levels, a larger sample could potentially reveal additional patterns. While our qualitative approach through conducting semistructured interviews provided rich insights into website owners’ experiences and motivations, it could be complemented by quantitative analyses to enhance generalizability. In addition, while our broad inclusion of various website types, from content-based sites to e-commerce stores, ensured a comprehensive range of insights, it might have limited more granular insights into specific business models.

These limitations inform several promising research directions. First, longitudinal analysis could provide valuable insights into specific digital business models’ resilience and long-term viability, offering guidance for entrepreneurs and investors. Such research should consider how these models interact with and contribute to the broader digital entrepreneurial ecosystem, as conceptualized by Sussan and Acs (2017).

Second, future research should focus on profiling website buyers, exploring their personas and comparing them to typical business buyers in ETA. In this respect, it would be useful to analyze website buyers’ backgrounds, motivations, strategies and succession plans. Understanding such characteristics could provide valuable insights into how they approach digital acquisitions and the unique considerations that they bring to the market.

Third, future research should examine share acquisitions and asset purchases as the two main types of acquisitions, including how they differ in the context of digital businesses. While our study did not explicitly differentiate between them, each carries distinct risks, liabilities and strategic implications. Asset purchases typically involve acquiring specific digital assets (e.g. websites and domain names) without inheriting broader liabilities, whereas share acquisitions involve taking on the entire company, including debts. Future research should explore how the characteristics of share and asset acquisitions influence the acquisition process and outcomes for digital businesses, particularly web-based SMEs.

Finally, investigating the impact of digital ETA on local and global communities would be valuable. This could be achieved by exploring how the acquisition and growth of web-based businesses affect employment patterns, skill development and economic growth in both the physical locations where these businesses are based and the online communities that they serve.

These research directions address the evolving trends in digital entrepreneurship and the specific characteristics of the ETA phenomenon, promising to provide actionable insights for entrepreneurs and investors. Moreover, they align with the growing need to understand the complex interactions within the entrepreneurial ecosystem and its impacts on various communities, both online and offline.

While ETA has been widely recognized as a promising solution to the looming succession crisis (Dennis and Laseca, 2016; Nows, 2021) and its application in traditional businesses has gained traction, the potential of ETA in the digital realm—particularly in the acquisition of web-based SMEs—has been largely overlooked. This paper argues that the unique strengths of digital businesses represent a compelling yet underexplored opportunity for entrepreneurs seeking to embark on the ETA journey.

Our research expands the understanding of ETA by applying it to the digital context. The global reach of web-based SMEs offers a distinct advantage in the ETA landscape. Our research has shown that many of these digital businesses serve international audiences, transcending geographical boundaries in ways that traditional businesses often cannot. Coupled with the potential for local economic impact through work opportunities and partnerships with physical businesses, this global reach positions digital ETA as a powerful tool for economic development and entrepreneurial growth. These findings contribute to the ongoing debate about the spatial dimension of entrepreneurship in the digital age. While some scholars argue that digitization is reducing spatial dependence (Autio et al., 2018), our findings align more closely with the perspective of Acs et al. (2017a, 2017b), Cavallo et al. (2019), Florida et al. (2018), who maintain that the local dimension remains crucial for investigating entrepreneurship. We argue that digital ETA exemplifies what Sussan and Acs (2017) described as a virtuous and reinforcing cycle between the biotic and abiotic components of the entrepreneurial ecosystem. In this context, the global reach of digital businesses does not negate local importance; rather, successful businesses with proven business models that scale globally can bring value back to the local arena. This dynamic demonstrates how digital ETA can foster global expansion and enrich the local ecosystem, highlighting its potential as a catalyst for economic development and entrepreneurial growth.

Our study further contributes to the broader entrepreneurial ecosystem theory. By analyzing the personas of digital entrepreneurs and their assets, we shed light on the diverse nature of digital entrepreneurship, focusing on scalable businesses that create value through digital technologies. We have found that website owners come from varied backgrounds, aligning with Giones and Brem’s (2017) characterization of digital entrepreneurship. This diversity facilitates a rich exchange of knowledge and skills when businesses change hands through ETA. The transfer of expertise benefits the individual entrepreneurs involved and fosters innovation and resilience within the digital business community as a whole (Pittz and Hertz, 2018). Our findings contribute to the ongoing discussion about the digital entrepreneurial ecosystem as conceptualized by Sussan and Acs (2017), providing empirical evidence of the broad spectrum of actors involved in digital entrepreneurship.

Moreover, our research sheds light on the distinct characteristics of web-based SMEs that make them attractive targets for ETA. These digital businesses’ scalability, lower initial investment and diverse revenue streams offer compelling advantages over traditional brick-and-mortar enterprises. While previous research has extensively examined how traditional SMEs adopt and implement digital technologies and information and communication technology capabilities (Cenamor et al., 2019; Parida and Örtqvist, 2015), our study extends this work by focusing specifically on entrepreneurial SMEs that are digital by nature.

Our research offers valuable insights for practitioners engaged in digital ETA. We provide a comprehensive framework of key considerations and recommendations to support practitioners in their website evaluation process (see Table 2). This framework synthesizes the insights gained from our research with established website owners and offers a structured approach to website acquisition assessment. Practitioners should leverage various deal sources when searching for potential websites to acquire, whereby platforms such as FEInternational.com, Flippa.com and EmpireFlippers.com offer a wide range of established online businesses for sale, catering to different niches, sizes and price points (Shepard, 2019). These platforms provide detailed listings, performance data and due diligence materials, facilitating the search and evaluation process for potential acquirers. In addition, technology-focused business brokers can be valuable resources for identifying off-market opportunities and navigating the intricacies of website acquisitions.

However, our research reveals that successful digital ETA extends beyond finding a suitable target. The digital landscape’s volatility necessitates focusing on businesses with diversified traffic sources and revenue streams, mirroring risk mitigation strategies used in traditional business acquisitions. Prospective buyers should pay particular attention to the unique value of digital assets, which often lies in their brand identity and engaged user communities. The preservation and growth of these elements post-acquisition are paramount to maintaining the business’s value proposition. Furthermore, our findings highlight the critical impact of rapidly evolving technology—particularly AI and privacy regulations—on digital businesses. Assessing a website’s adaptability to these changes is crucial for ensuring long-term viability. Finally, successful digital ETA strategies should leverage the inherent global reach in many web-based SMEs while also exploring opportunities for local partnerships or impact, reflecting their dual nature as global and locally relevant entities.

One of the most compelling insights from our research is the importance of understanding the seller’s motivations and the website’s unique selling proposition when considering an acquisition. Our findings reveal that website owners often have deep emotional connections to their digital ventures, viewing them as extensions of their personal and professional identities. Practitioners seeking to acquire a web-based business should approach negotiations with empathy and clearly understand the seller’s goals and expectations. Buyers can increase the likelihood of a successful transaction and ensure a smoother ownership transition by tailoring their offers and post-acquisition plans to align with the seller’s vision.

Entrepreneurs can better navigate the complexities of the digital marketplace by considering these factors throughout the acquisition process, from the initial search to the post-acquisition strategy. As this landscape continues to develop, those who are well-prepared, adaptable and committed to effectively implementing these strategies will be best positioned to seize the opportunities presented through digital entrepreneurship. Moreover, by pursuing ETA through website acquisition, practitioners can transform established digital assets into sustainable enterprises while simultaneously addressing the broader succession crisis in the entrepreneurial landscape. This pathway offers individual entrepreneurs a viable route to business ownership and ensures the continuity and evolution of valuable digital communities and content. The future of digital ETA thus represents a promising intersection of entrepreneurial opportunity and ecosystem sustainability, offering a structured approach to business acquisition that can benefit individual entrepreneurs and the broader digital economy.

The authors are deeply grateful to the interview partners who generously contributed their time and insights to this empirical research.

Declaration of competing interest: The authors declare that there is no conflict of interest.

Research funding: The authors declare that no funding was used for this research.