Jonathan Jay speaks with software business owner Kris Bark about targeting acquisitions, building seller outreach at scale, structuring deferred consideration, and using deal flow to create a larger group without relying on personal cash.
Listen to the EpisodeEpisode 162 | Runtime: 23:42 | Audio Episode
Hear the full conversation with Kris Bark on acquisition outreach, software sector strategy, deferred deal structures, and building a pipeline of off-market acquisition opportunities.
Three practical lessons from a business owner moving from organic growth to acquisition led expansion.
Kris explains how direct letters and hundreds of owner conversations gave his team market data, pattern recognition, and a measurable acquisition pipeline.
The conversation shifts from chasing the lowest multiple to asking whether a deal can be funded through deferred payments, available cash, and sensible consideration terms.
Buyers who understand their target market can filter unsuitable companies faster, avoid emotional bidding, and make offers based on facts rather than seller expectations.
In this episode, Jonathan Jay interviews Kris Bark, a software business owner who has spent years considering acquisitions and moved decisively after buying out his business partner. Kris explains how his original view of acquisitions changed from bank loans and self funded purchases to a structured approach based on seller conversations, deal flow, and financing creativity.
The discussion covers how Kris assessed competitors, complementary businesses, marketing agencies, web development companies, ecommerce businesses, and product based companies before refining his acquisition strategy. He shares why software businesses often carry high valuation expectations, why owner dependence matters, and how focused market knowledge helps buyers decide which opportunities deserve attention.
Kris also breaks down the numbers behind his outreach, including thousands of letters, hundreds of seller conversations, multiple offers, agreed deals, and completed acquisitions. The episode is a direct case study in using deferred consideration, target market data, disciplined valuation, and persistent follow up to build a pipeline capable of supporting a multi acquisition group strategy.
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