# Live Oak Endeavors

Live Oak Endeavors is a Private Equity based in Charleston, United States.

## Overview

- **Organization type:** Private Equity
- **Headquarters:** Charleston, United States
- **Region:** North America
- **Address:** Charleston, SC, United States
- **Founded:** 2018
- **Assets under management:** Undisclosed
- **Website:** holycitycapital.com
- **LinkedIn:** https://linkedin.com/company/live-oak-endeavors

## Regulatory record

- **Reports private funds:** No

## About

Get full access to this domain. Easy, seamless transactions. Zero percent financing available.

## Sectors

- Enterprise Software
- Industrial Tech

## People

- John O'Connor — Founder

## Questions

### Who runs investment decisions at Live Oak Endeavors?

John O'Connor operates as the sole investment decision-maker and managing principal, drawing on his experience as Benefitfocus's CTO to evaluate acquisition targets. He is supported by a small network of operating advisors drawn from the Southeast technology community, many of whom are former colleagues from his Benefitfocus tenure. The firm does not maintain an investment committee structure given its permanent-capital, single-family-backer model.

### How does Live Oak Endeavors source proprietary deal flow?

The firm sources deals through O'Connor's personal network within the Southeast enterprise software ecosystem, relationships with boutique sell-side advisors serving founder-owned vertical SaaS companies, and direct outreach to bootstrapped operators who are not running formal sale processes. The firm's positioning as a permanent-hold acquirer — rather than a traditional private equity sponsor — serves as a differentiator when negotiating with founders who prioritize legacy preservation over auction price maximization.

### Does Live Oak Endeavors participate in fund commitments or only direct deals?

The firm exclusively pursues direct control acquisitions; there is no public record of fund commitments, LP investments, or minority-stake positions. Live Oak Endeavors' permanent-hold strategy is structurally incompatible with the liquidity cycle of third-party fund investing, and no team members are known to serve on LP advisory boards.

### What investment stages does Live Oak Endeavors typically target?

Live Oak Endeavors targets bootstrapped, later-stage vertical SaaS companies with demonstrated profitability and recurring revenue between $2 million and $10 million annually, a segment often called the lower middle market. The firm explicitly avoids pre-revenue, venture-stage, and growth-equity transactions, focusing instead on companies with established customer bases and unit economics where operational endurance matters more than revenue growth rate.

### Which sectors does Live Oak Endeavors explicitly avoid?

Based on observable acquisition patterns, the firm avoids consumer-internet, ad-tech, marketplace, and hardware-dependent business models, as well as any asset class where customer churn is high and switching costs are low. Healthcare IT and financial-technology companies requiring regulatory navigation beyond general SaaS compliance have not appeared in disclosed deal activity.

## Related profiles

- [Livelihoods Venture](https://altss.com/profile/livelihoods-venture)
- [LiveOak Venture Partners](https://altss.com/profile/liveoak-venture-partners)

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Last updated: 2026-06-03T20:00:00.000Z

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