Aug. 12, 2024

AI-Powered Valuation: How AI is Revolutionizing the M&A Process with Simon Leroux

E237: AI-Powered Valuation: How AI is Revolutionizing the M&A Process with Simon Leroux - Watch Here

About the Guest(s):

Simon Leroux is a seasoned entrepreneur and current CEO and Founder of Optionality, an AI-driven platform focused on the mergers and acquisitions space. With a rich history in building and exiting businesses, Simon successfully bootstrapped his last startup, Gazelle AI, and led it to an acquisition by KKR. He holds extensive experience in e-commerce, artificial intelligence, and data analytics. Post-exit, Simon joined Inovia Capital as an Entrepreneur in Residence (EIR), where he leveraged his expertise to support promising startups.

Episode Summary:

In this insightful episode of the How2Exit Podcast, host Ronald Skelton sits down with Simon Leroux, a serial entrepreneur and CEO of Optionality. Simon shares his journey from bootstrapping his previous venture, Gazelle AI, through its acquisition by KKR, to founding his latest AI-powered platform, Optionality. The podcast delves deep into the critical inquiries every business owner faces: the actual worth of their business, the best timing for a sale, and the steps needed to maximize enterprise value.

Simon discusses the intricacies of using AI in Optionality to assist advisors in the M\&A space. He highlights how this tool automates much of the time-consuming research required for valuations, making it a game-changer for advisors. Through the platform, significant efficiencies are realized, enabling advisors to deliver faster and more accurate valuations based on comprehensive data analysis. The episode also underscores the importance of building strategic partnerships and stresses the need for business owners to start planning for an exit well in advance.

Key Takeaways:

  • Optionality in Business Transactions: Simon stresses the importance of having multiple exit options to maximize enterprise value.
  • Proactive Advisor Engagement: Business owners should engage advisors early to plan for exits effectively.
  • AI-Powered Efficiency: Simon explains how Optionality leverages AI to streamline the process of business valuations for advisors.
  • Strategic Relationships: Building long-term relationships with potential acquirers and strategic partners can significantly impact exit success.
  • Tailored Valuation Models: The platform's ability to use multiple valuation methods ensures a more comprehensive and accurate business assessment.

Notable Quotes:

  1. "Optionality is what gives you value. If you're in control and have options, this is where you're going to maximize your enterprise value." - Simon Leroux
  2. "The problem that I've seen in this market is that the business owners are waiting way too long to have those conversations." - Simon Leroux
  3. "Our platform is designed to get that initial enterprise value estimate to provide an initial assessment and options for business owners." - Simon Leroux
  4. "AI is your co-pilot; it makes the advisors more efficient, having more powerful strategic conversations with their clients." - Simon Leroux
  5. "Find an advisor that knows your space, has a track record in your industry, and your company size." - Simon Leroux

Article: 

M&A Insights: The Power of Optionality and Proactive Advisory

Key Takeaways

  • Proactive Advisory: Engaging a knowledgeable advisor early can significantly affect the value and options available during an exit.
  • Leveraging AI in M&A: AI tools can streamline the M&A process, offering accurate valuations and strategic insights.
  • Importance of Optionality: Having multiple potential buyers and strategic partners enhances enterprise value and deal success chances.

Embracing AI for Efficient M&A Valuations

Artificial intelligence (AI) is revolutionizing the way mergers and acquisitions (M&A) are conducted, and Simon Leroux, founder of Optionality, is at the forefront of this transformation. In a recent discussion, Simon delved into how his new AI tool is designed to assist advisors in providing accurate business valuations and strategic insights.

The Role of AI in M&A

Optionality, according to Simon, is built on the backbone of various large language models (LLMs) such as OpenAI, Google's Gemini, and CoHere. These models are paramount in analyzing vast amounts of data quickly and efficiently. As Simon mentioned, “We do a live search on that website, build a pitch deck, and generate comparables using AI semantic and vectorization.”

This approach allows for precise and immediate insights, significantly reducing the time advisors typically spend on manual research. Traditionally, analysts could spend up to 10 hours gathering and analyzing data to present a viable valuation. With Optionality, these insights are generated in minutes, enabling advisors to focus more on strategic discussions.

Enhancing Decision Making with AI

Simon also emphasized the predictive capabilities of AI, stating, “We are using machine learning algorithms to predict the likelihood of a company to sell and its future enterprise valuation.” This predictive power can inform advisors about the optimal timing for a sale, thus maximizing the business’s value.

The potential impact of such AI tools is immense. They not only streamline the valuation process but also provide a robust foundation for strategic decision-making, facilitating better outcomes for business owners.

The Crucial Role of Proactive Advisory

One of the standout themes from Simon’s discussion is the critical importance of proactive advisory in the M&A process. Many business owners wait too long to engage with advisors, leading to rushed decisions and potentially unfavorable outcomes.

Early Engagement with Advisors

Simon highlighted the significance of early and continuous engagement with knowledgeable advisors. He pointed out, “The problem that I've seen is that the business owners are waiting way too long to have those conversations.” By involving advisors well ahead of a potential sale, business owners can better prepare and align their strategies with market demands.

Moreover, choosing the right advisor is paramount. As Simon suggested, “Pick up an advisor that knows your space, have a track record in your industry and your company size.” Advisors with specific industry expertise can provide tailored insights, helping to navigate the complexities of the M&A landscape more effectively.

Building Relationships Early

Another critical aspect Simon discussed is fostering early relationships with potential buyers. He shared an insightful approach where founders engage in conversations with potential acquirers years before planning to sell. This strategy not only builds rapport but also aligns product development with market needs.

He recounted, “You should be surprised at how open they are to having those type of calls. Say, Hey, look, I'm nowhere near ready to sell my company. But, you know, in the long run, I'd like to work with a company like yours.”

Maximizing Enterprise Value through Optionality

Optionality – the concept of having multiple options – is a recurring theme in Simon’s narrative. He believes that having various strategic options significantly enhances a company's value and improves the likelihood of a successful exit.

Strategic Partnerships and Market Fit

In Simon’s view, creating strategic partnerships early on is crucial. He emphasized the importance of building relationships with key customers, suppliers, and partners to explore potential synergies. This proactive approach can lead to higher multiples and better valuation outcomes. Simon aptly put it, “Can I create a collaboration platform where the business owner can be more proactive?”

Furthermore, being informed about industry-specific valuation models and market conditions is vital. While traditional real estate valuation methods rely on comparable sales, business valuations require a more nuanced approach. Simon’s method involves a mix of financial methods and market insights to provide a realistic valuation, thus offering a comprehensive picture to stakeholders.

Realistic Expectations and Preparation

Simon also stressed the necessity of managing expectations and preparing meticulously for an exit. He mentioned, “The advisor’s role is to explain that, while comps give a ballpark figure, the real value lies in operational and financial metrics, market conditions, and strategic fit.”

Advisors leveraging tools like Optionality can present a clearer picture, enabling business owners to understand their true market value and strategically position themselves for acquisition. This dual focus on realistic valuation and strategic preparation ensures that business owners are not only ready to exit but are doing so on terms that maximize their returns.


Optionality and proactive advisory are not just buzzwords but vital strategies in the M&A landscape. By embracing AI tools for efficient and accurate valuations, engaging advisors early, and building strategic relationships, business owners can navigate their exit journeys more effectively. This proactive, data-driven approach empowers both advisors and business owners, ensuring better outcomes and maximizing enterprise value. Whether you're a founder or advisor, the insights shared by Simon Leroux offer invaluable guidance on rethinking the traditional M&A paradigm.

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