In a conversation with Arthur Rothrock on The Litigator's Path, Hollander explains how he and co-managing partner Richard Golubow restructured their firm's leadership and compensation after years of inequity among senior partners, why he treats every potential Chapter 11 client like an underwriting decision, how he expanded into New York and New Jersey to follow shifting bankruptcy venue rules, and what he looks for – and watches out for – when hiring associates into a practice that demands both litigation and business skills. The thread running through all of it: building a durable law practice requires the same clear-eyed financial discipline he brings to his clients' balance sheets.
How Hollander Evaluates Whether a Chapter 11 Client Can Actually Pay
Most corporate debtor attorneys face a version of the contingency-fee problem: the client is in financial distress by definition, and the firm may work a case for a year or two before seeing a dollar. Hollander describes his firm as "contingency lawyers without the upside" – billing hourly but subject to court review and creditor objections, with no premium if the case succeeds. Katie Deamer runs a parallel dual practice – commercial litigation alongside creditor-focused bankruptcy work – and uses prejudgment writs of attachment to protect clients before a filing can wipe out their position.
His intake process is part legal analysis, part underwriting. Before accepting a case, Hollander evaluates the debtor's assets, cash flow, secured creditor positions, likelihood of obtaining financing, and realistic sale or reorganization prospects. Retainer size is calibrated to what the company can actually afford. In some cases, he takes the engagement with little or no retainer at all – and says those cases have paid off "almost without exception" because he looked beyond the surface numbers.
One recent example: a client's assisted living facility needed $24 million in financing that ten intermediaries across the country failed to secure. Hollander kept calling lenders directly until he found one willing to fund the deal. The client kept the facility and is now finishing development. That kind of persistence, he says, is inseparable from the financial analysis – knowing a case is viable gives him the conviction to keep pushing when the conventional channels dry up.
He is equally blunt about client dishonesty. Quoting advice from his first job at Coopers & Lybrand – "clients lie, they all lie, don't ever forget that" – Hollander says exaggeration or denial doesn't automatically disqualify a client, but it changes how he manages the engagement. He recommends The Sociopath Next Door and notes, without irony, that CEOs and lawyers top the list of professions with the highest rates of sociopathic traits.
Why Hollander Restructured His Firm's Compensation – and Moved to a Smaller House to Do It
Hollander joined what was then Winthrop Couchot as an associate in 2001, drawn by the firm's exclusive corporate debtor practice and its reputation. But over the years, a familiar small-firm tension emerged: senior partners shifted toward origination and stopped working cases, while Hollander and a handful of others carried the workload. On cases he touched, realization rates exceeded 90%; on one senior partner's cases without his involvement, they hovered around 50%.
He developed a compensation formula to address the imbalance and initially met resistance. His next move was strategic and personal: he downsized his home to reduce his overhead, making his threat to leave financially credible. "You got to be willing, ready, and able to act on it," he says. "If it's not real, it's like not following through on a baseball swing."
He partnered with Richard Golubow, and the two told the senior partners they would leave unless the firm adopted the new structure. The seniors relented, eventually departing on their own. The firm converted from a professional corporation to an LLP – a structure Hollander says multiple advisors had long recommended – drafted new governing documents, and put Hollander and Golubow's names on the door. The result: a transparent, formula-driven compensation system where origination credit, billable work, and pay are all visible and predictable. Year-end, once a source of tension and backroom negotiation, became uneventful. "Everyone knows what they're getting," Hollander says. "There's no hidden."
Hollander's Approach to Hiring Associates for a Practice That Blends Litigation, Transactions, and Business Advice
Winthrop Golubow Hollander currently has six attorneys and no associates – a gap the firm is actively trying to fill through headhunters. The difficulty, Hollander explains, is that business litigation in the corporate debtor context demands a combination of skills rarely found in a single candidate: litigation ability, transactional knowledge, business judgment, people skills, and the discipline to work efficiently without the cushion of a large-firm staffing model.
He recalls hiring an attorney from Milbank whose instinct was to "just bill." That mindset, Hollander says, is incompatible with a boutique where economic analysis drives every decision. "If I can solve a problem in one minute, I'll do that all day long. There's enough problems to solve. I don't need to milk anything."
On compensation, the firm offers flexibility. Some associates want a straight salary; others prefer a hybrid with origination credit. Hollander is willing to share in what associates bring in, though he draws the line at candidates who want "guaranteed and all the upside but no downside." Bonuses are discretionary but real, and the firm encourages associates to originate early. The hiring trigger is more instinct than formula – when the partners feel stretched and the pipeline looks durable, they start looking.
How Shifting Bankruptcy Venue Rules Pushed Hollander Into Multi-State Practice
California's share of major Chapter 11 filings shrank after courts began allowing Delaware-incorporated companies to file in Delaware rather than where their assets or headquarters were located. With large cases gravitating toward Delaware and New York, Hollander expanded. He is now admitted in New York and New Jersey – the latter becoming what he calls "the newest hotbed" for bankruptcy filings – and is building a referral network there through in-person meetings and local counsel partnerships.
The expansion is practical, not aspirational. Hollander is not trying to build a large firm. His ten-to-fifteen-year plan is to find and train successors who can carry a brand that has been operating since the 1970s. "The brand is spectacular," he says. "It's been around since the 70s. We have an exclusive corporate debtor work practice. If anyone wants that, they'll try to find it. It's extremely hard."
What Hollander Gets Right About Work-Life Boundaries – and Why It Starts at 5 a.m.
Hollander describes himself as a "24-7 guy," but the details tell a different story. He was home for dinner every night while his children were growing up. He coached their teams. He takes at least one two-week international vacation every year and has done so since his first job. His method for protecting gym time: 5 a.m., before anyone can schedule over it.
The key, he says, is that boundaries only hold if your output removes any basis for questioning them. "If you put in your time and you're valuable, have more confidence in yourself," he says. No employer or client has ever challenged his schedule. He credits his wife as a full partner in his career decisions – from the move to a smaller house to the decision to push for firm leadership – and says that spousal alignment is one of the least-discussed factors in attorney career satisfaction.
What Litigators Can Take Away
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Hollander vets every potential Chapter 11 engagement like an underwriter, evaluating assets, cash flow, secured creditor rights, and financing prospects before accepting – and is willing to take cases with minimal retainer if the deeper analysis supports it, a discipline that has paid off across decades of practice.
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When he needed to force a compensation restructuring at his firm, Hollander made his leverage credible by downsizing his home first – reducing personal overhead so that walking away was a real option, not a bluff, which is the only way he believes ultimatums work in partnership disputes.
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His firm's transparent, formula-driven compensation system eliminated the year-end negotiation battles that plagued the old corporate structure; every partner knows exactly what origination, billing, and effort produce, which Hollander says built the trust that holds the partnership together.
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Hollander's primary source of new business is not advertising or trade associations but opposing counsel and other attorneys he's impressed during representations – including one lawyer who hired him multiple times after Hollander won a $420,000 sanction award against him and his client.
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He protects personal time by scheduling it where no one can overwrite it – gym at 5 a.m., vacations booked and committed to in advance – and says the strategy only works if your billable output is high enough that no one has standing to question it.
Listen to the Full Episode
Garrick Hollander's full conversation with Arthur Rothrock covers more ground than we could fit here – including his early entrepreneurial ventures, the economics of small-firm Chapter 11 practice, and why he thinks most lawyers spend too much time on issues that will never materialize. Listen on Spotify or Apple Podcasts. To learn how Legion helps litigators draft pleadings, discovery, and motions in minutes, visit legion.law.