Twenty-Five Years of TOBIN

This is what I love about entrepreneurs. We are confident, unburdened, and full of hope. I had the benefit of starting my firm at the dawn of the Internet, but it seems impossible now that I accomplished all of that without the help of AI. Apparently, it can be done the hard way. I look back on my very steep learning curve and marvel at how massively flattened it can become with this new technology. Even so, when I started my firm, I had plenty of imagination, resilience and flexibility. I had my innate stubbornness, tempered by all of the requisite naïveté to allow myself to attempt something this improbable. And I was unconventional enough to be a woman who dared to found her own investment bank, in an industry dominated by men, just a few weeks after the turn of the new millennium.

Reaching our twenty-fifth anniversary as a firm this month feels like a geological marker: a quarter-century of layers of transactions, crises, reinventions and people who shaped our business, its culture, and, in all honesty, shaped me. Some start-up companies become empires. Some ignite, collapse and leave dramatic case studies behind. Others, like TOBIN, simply endure quietly and steadily, unwilling to disappear, refining themselves year after year. Survival in the capital markets industry is, in its own right, a form of achievement.

Origins

TOBIN is the only investment bank and broker-dealer in the United States solely owned by a woman. The rarity still astonishes me. I genuinely believed that by now, twenty-five years later, women would own a meaningful share of investment banking firms and broker dealers. I thought we would be prominent in the execution of financial transactions across the country. Progress has been slower than expected, and in some respects more fragile than we like to admit.

Of course, not everyone greeted my new firm in 2001 with enthusiasm. Women who build in male-dominant environments know this experience intimately: the quiet resistance, the overt patronizing, and in a few memorable cases, the deliberate attempts to undermine. I learned early that the absence of anyone’s belief was not a verdict. It was simply data. The firm’s longevity is the response.

On the other side of this spectrum sits an immense cast of supporters; clients, colleagues, advisors, employees, interns, relatives and friends – whose support mattered more than they may ever know. Their trust is woven into TOBIN’s structure. Across twenty-five years, those relationships have been far more consequential than any single transaction.

There were remarkable people who helped TOBIN get its start. Marcia jumped with joy at the ladies’ lunch on the day I announced. Jeff brought our first client. Cy insisted on a new business line. Jen wrote mailers. Lesley made cold calls. Greg was among our first analysts.  These folks, and many others like them, sustained this firm through late-night financial model renovations, difficult conversations with attorneys and regulators, and the unceasing work of protecting clients’ interests – all while raising a family, sustaining a marriage and navigating the peculiar choreography of entrepreneurial life.

Formation

If I’m candid (you know I usually am) founding and running this independent investment bank and broker/dealer has been metamorphic. Not in a tragic nor heroic sense, but in the way that slyly rearranges a person’s head and heart. Founding and operating TOBIN has also been profoundly rewarding. The breadth of experience, the extensive view of the capital markets, the trust of clients and the opportunity to build a home for talented people – these are the architecture of a unique career that I certainly would choose again.

I was raising three children when I founded the firm, with my husband watching from across the table. While TOBIN has always been distinctly mine, the idea was his – proposed fifteen months after he founded his own architecture practice for the second time. I initially resisted. Then I realized he was right. I was never going to survive inside corporate investment banking. My husband broke me out and he has supported every turn of this adventure, even serving as our (largely invisible) CTO. The Wall Street Journal recently reported that businesses founded by couples succeed more often than those created by solopreneurs. Over these past twenty-five years, my architect husband has been a steady life partner. I am so grateful.

All three of our now grown children and their significant others are stable, grounded and forging their own trajectories, each with their own dose of entrepreneurship. One of them, Jon Tobin, was just five years old when I founded the firm, attending pre-K classes three days a week and starting kindergarten just seven months into the life of the firm and just a couple of short weeks before the events of 9/11. Today, he is a college graduate and a vice president at TOBIN. Keeping my family intact, and meaningfully involved in the firm, amidst  incredibly volatile market cycles, regulatory shifts and economic tremors was its own high-wire act that makes me beam with immense pride. The semblance of equilibrium that emerged over time became our family’s version of normal. It did not resemble anyone else’s.  The fact that I didn’t lose myself – or them – along the way seems almost impossible to me.

Like many entrepreneurs, I cried myself to sleep more than once. Sometimes I don’t sleep at all. Over time, I have learned some durable truths: accept what cannot be changed and move forward without resentment; understand that being perceived as the underdog can be liberating; hold fast to convictions like fairness, kindness, empathy, and courtesy, especially when they are unfashionable. Embracing all of these, along with the uncertainty, unceasing endurance, and frequent wobbles,  I can easily confess this without qualification: I truly love what I do.

I love the work itself. I love the thinking. I love the responsibility. I love the privilege of being trusted with decisions that matter to real people, families, and businesses. I love building something durable in a world that often rewards image over substance.

I think often about the women who might read this, women considering their own firms, or are already standing in the early, volatile years of entrepreneurship. I want to be deliberate here, not performatively encouraging, but grounded.

It is possible. It is categorically possible to build a firm in finance as a woman, to remain intact as a human, to raise a family, to sustain a marriage, to ignore the trolls and naysayers, to lead with clarity and integrity, to withstand the unrelenting turbulence of this industry and to emerge with a sense of self stronger than when you began. But, you cannot do it by seeking universal approval. Approval is elusive, brittle and often misinformed. What sustains you is a mind steady enough to operate under biased scrutiny, sharp enough to solve complex problems, and flexible enough to recalibrate when the ground shifts.

As you undergo your adventure, you will need to discern whose voices matter. A surprising number will not. One of the most important lessons I’ve learned is that what others think about me is typically not my business.  Feedback from clients matters. Intentions matter. Everything else is noise.

There is no singular blueprint for your journey. My path unfolded through persistence, a refusal – probably an inability – to retreat, and an unyielding commitment to client service. I built TOBIN on the belief that competence, ethics, and clarity are non-negotiable. That belief continues to guide every decision we make.

Continuity

Looking forward, the next twenty-five years of TOBIN will not be a reprise of the first. The firm is more capable, more precise, more knowledgeable and more driven than ever. In a world changing faster than any of us anticipated, institutions grounded in judgment, fairness, and human discernment matter deeply. TOBIN intends to remain a bedrock for our clients; steady, principled, and durable, regardless of how the landscape shifts.  I intend to work throughout this next chapter, remaining with focus, resolve, and confidence in what profound experience can offer a turbulent world.

To the clients who have trusted TOBIN, the colleagues who have stood with us, the allies who have offered wisdom and my family who has walked through every volatile cycle: thank you. The endurance of this firm is a community achievement.

And to the women and future founders who may be reading this – quietly weighing whether you could do something similar – please know this: you can. The door will not open for you. You will have to build that door, and the structure behind it. And then, your entire complex will stand.

Here’s to the next quarter century. I intend for it to be even more formidable.