app01 Tue, 14 Jul 2026 02:16:37 +0000 Fireside (https://fireside.fm) FEI Podcast - Episodes Tagged with “Entrepreneurship” https://feipodcast.fireside.fm/tags/entrepreneurship Mon, 13 Jul 2026 12:00:00 -0400 Financial Executives International presents the FEI Podcast: an audio digest focusing on the ideas and strategies in finance and accounting. en-us episodic Discussions and thought-provoking ideas from Financial Executives International Financial Executives International Financial Executives International presents the FEI Podcast: an audio digest focusing on the ideas and strategies in finance and accounting. no business, finance, accounting, strategy Financial Executives International info@financialexecutives.org From CPA to Founder: Why This CFO Says It's Time to Take More Risk – with Chrissy O'Hara https://feipodcast.fireside.fm/186 4306e205-0142-418f-a043-b28629241f69 Mon, 13 Jul 2026 12:00:00 -0400 Financial Executives International full Financial Executives International Chrissy O'Hara, CFO of SoftLedger, shares what entrepreneurial freedom really costs and why more finance and accounting professionals need to take bigger risks. 33:20 no <p>What happens when a CFO trades the structure of a traditional corporate finance career for the unpredictability of a startup? In this episode, recorded live at FEI's <em><strong>Financial Leaders Forum</strong></em> in San Antonio, host Heather Cole sits down with <strong>Chrissy O'Hara, CFO of SoftLedger</strong>, to talk about the real tradeoffs of entrepreneurial freedom: cash flow stress, family members who keep asking when the “real job” is coming, and the discipline it takes to keep pivoting when plans change. O'Hara also shares how she learned to let go of the perfectionism her CPA training instilled, how she and her team use AI tools like Claude and ChatGPT day to day, and why she believes more finance and accounting professionals need to step into entrepreneurship and be in the room shaping the next generation of tools, rather than waiting for someone else to make those decisions for them. Special Guest: Chrissy O'Hara.</p> CFO entrepreneurship, startup CFO, SoftLedger, career transition, financial leadership, accounting software, AI in accounting, FEI Podcast, cash flow management, FP&A, risk taking, financial executives What happens when a CFO trades the structure of a traditional corporate finance career for the unpredictability of a startup? In this episode, recorded live at FEI's Financial Leaders Forum in San Antonio, host Heather Cole sits down with Chrissy O'Hara, CFO of SoftLedger, to talk about the real tradeoffs of entrepreneurial freedom: cash flow stress, family members who keep asking when the “real job” is coming, and the discipline it takes to keep pivoting when plans change. O'Hara also shares how she learned to let go of the perfectionism her CPA training instilled, how she and her team use AI tools like Claude and ChatGPT day to day, and why she believes more finance and accounting professionals need to step into entrepreneurship and be in the room shaping the next generation of tools, rather than waiting for someone else to make those decisions for them.

Special Guest: Chrissy O'Hara.

]]> What happens when a CFO trades the structure of a traditional corporate finance career for the unpredictability of a startup? In this episode, recorded live at FEI's Financial Leaders Forum in San Antonio, host Heather Cole sits down with Chrissy O'Hara, CFO of SoftLedger, to talk about the real tradeoffs of entrepreneurial freedom: cash flow stress, family members who keep asking when the “real job” is coming, and the discipline it takes to keep pivoting when plans change. O'Hara also shares how she learned to let go of the perfectionism her CPA training instilled, how she and her team use AI tools like Claude and ChatGPT day to day, and why she believes more finance and accounting professionals need to step into entrepreneurship and be in the room shaping the next generation of tools, rather than waiting for someone else to make those decisions for them.

Special Guest: Chrissy O'Hara.

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