Cyrus Symoom: From Search to Scale – Navigating the Journey of Entrepreneurship Through Acquisition

portrait of Cyrus Symoom
Cyrus Symoom is the Co-CEO of Clariti, a software company for state and local governments, to delve deep into the world of entrepreneurship through acquisition (ETA). Cyrus shares his incredible journey of purchasing Clariti through a self-funded search at just 26 years old, highlighting the challenges and triumphs of acquiring and scaling a tech company in the Canadian landscape. Cyrus also explains how he approached his six month search process and raised eight-figure equity financing, the strategic and cultural shifts made to transform a 20-person company into a 120-employee leader in its field, the importance of low ego and high humility in leading an organization through significant changes, and why more Canadians should consider ETA as a career path. Whether you're an aspiring entrepreneur, a seasoned investor, or simply curious about ETA, this episode offers practical advice, personal anecdotes, and strategic insights into building a thriving business.

5 Key Takeaways: 

  1. Start with a Learning Mindset: Whether you’re exploring search funds or acquiring an existing business, a learning mindset are essential. Leverage existing resources and talk to experienced searchers to expand your knowledge.
  2. Partnership Benefits: Teaming up with someone you trust can provide emotional and operational support, which is crucial during challenging entrepreneurial endeavours.
  3. Search Strategies: Using a multi-channel approach for searching acquisition targets, including cold outreach, brokers, and leveraging personal networks, can increase chances of success.
  4. Cultural and Strategic Shifts: Emphasizing low ego and high humility can lead to more effective leadership and smoother transitional periods after acquiring a business.
  5. Long-term Vision: Cyrus discusses the benefits of holding and growing a business long-term, rather than aiming for a quick sell-off, a new perspective on creating lasting value.

Show Notes

[00:00:59] Cyrus details the pivotal moments that piqued his interest in entrepreneurship through acquisition. A summer internship with Queen’s University alumni introduced him to mergers and acquisitions, while witnessing other young entrepreneurs investing in small businesses sparked his curiosity.

[00:02:37] Discovery of the search fund model and the journey of raising capital.

[00:03:54] Reflecting on his early days of exploring small businesses, Cyrus emphasizes the importance of humility and learning from others.

[00:06:39] Transitioning from investment banking to ETA and the role of work-integrated learning.

[00:08:00] Cyrus explains how he cold-emailed and reached out to 30-40 different searchers to learn more about ETA. 

[00:10:53] Decision to partner with a close friend for the search process and the dynamics of their collaboration.

[00:13:11] Cyrus shares the benefits of searching for businesses with a trusted partner. His best friend Jake’s complementary skill set and different personality type made the duo effective:

[00:17:07] Explanation of self-funded versus traditional search models in ETA.

[00:20:18] Discussing the psychological turmoil of a long search, Cyrus underscores the importance of setting internal KPIs and celebrating progress. He also advises adopting a curiosity mindset to stay engaged.

[00:25:54] The strategy of using multiple channels to search for acquisition opportunities.

[00:28:46] Cyrus and Jake approached their search methodically, using a combination of proprietary outreach, brokers, and leveraging their network. They ran an internship program that accelerated their search and ultimately discovered the Clariti opportunity through their network.

[00:33:24] Cyrus offers advice to searchers interested in acquiring tech companies and emphasizes the need to find a good revenue multiple that provides a margin of safety.

[00:38:17] Challenges and achievements in the first months after acquiring the company, transitioning to remote work during COVID-19.

[00:42:10] Cyrus recounts how his first 100 days were focused on communication, building relationships, and aligning the team on vision and culture.

[00:47:17] After building foundational trust, Cyrus and Jake focused Clariti on a single vertical—building permitting and community development—to differentiate the company.

[00:57:51] Discussion on long-term business operations and the evolution of ETA investment models.

[00:58:43] Cyrus encourages aspiring entrepreneurs not to wait for more experience and to take the leap into ETA