Deborah Jackson and the art of failing retirement

Deborah Jackson tried retirement. She joined nonprofit boards, explored her bucket list and discovered that being finished with Wall Street did not mean being finished with work. Her verdict, delivered with the economy of a banker closing a meeting: “I flunked retirement.” It is a useful place to begin with someone whose later career has involved persuading other people that they, too, have more to contribute.

Jackson had spent more than two decades raising capital. She knew the people who could get a meeting, the language that made a proposal legible and the difference between having an idea and having the money to pursue it. When she began mentoring women entrepreneurs, she encountered a familiar imbalance from a different seat. There were capable founders building companies. Getting capital to them was another matter.

Plum Alley grew out of that encounter. Today Jackson is its founder and CEO, a founding partner and a general partner of its first venture fund. Yet the more revealing job description might be the one she gave herself through her work: bringing people into an investment conversation they had previously watched from outside. The founders needed an audience. Some of the investors needed an invitation.

A childhood spent arriving

Jackson’s father worked for IBM. The family moved repeatedly around the United States, giving her plenty of practice at entering unfamiliar rooms. She has described that childhood as training in adaptability and resourcefulness. A new school offers an unromantic lesson in how networks operate: everyone else seems to know the rules before you have found the classroom.

She studied at Michigan State University and earned an MBA at Columbia Business School in 1980. Her undergraduate field was consumer economics; her graduate focus was finance. Before business school, she had worked as executive director of a government watchdog agency in Cambridge, Massachusetts. The public sector and the capital markets were both part of her education before entrepreneurship became the main event.

In 1980 she joined Goldman Sachs. Municipal finance was an early assignment. More than twenty years of capital raising followed, across public and private entities. That is a substantial apprenticeship in the practical business of making institutions possible. A financing plan has to survive other people’s questions. Enthusiasm is welcome at the table, but it cannot be the only thing on the menu.

The promotion that came with an excuse

Her account of an annual review at Goldman contains the sort of detail that makes a general argument suddenly personal. A boss told her she could run her division better than the man in charge, she recalled. Then came the reason she could not be promoted over him: what would he tell his wife, and how would it look?

Jackson also remembered male clients feeling comfortable asking her questions they were reluctant to put to male bankers. The two recollections sit awkwardly together. Being useful to a client did not automatically settle the question of who should lead. Competence could be recognized in one sentence and put aside in the next. She has not had to imagine how that feels.

Leaving Goldman required its own deliberation. She has said it took two years of evaluation before she departed with colleagues to start a boutique firm. The decision matters because her later work can look inevitable when reduced to a biography. It was a departure from security, weighed over time. Even a person who spends her career encouraging new ventures may take a while to start one.

“Great companies don’t just pop up.”

Deborah Jackson, 2015

Eighteen women, one weekend

By 2011, Jackson was helping build a different set of rooms. She founded JumpThru and co-founded Women Innovate Mobile with Kelly Hoey and Veronika Sonsev. The accelerator concentrated on women-founded mobile technology companies. Its focus was specific enough to act on: find founders working in a growing technical field and surround them with investment and mentorship.

There was also a weekend hackathon. Eighteen women came together and built an interactive game intended to raise awareness of human trafficking. They researched an unfamiliar subject, divided up the work and produced a functioning project in forty-eight hours. Jackson later counted the experience among the moments that stayed with her. There was something persuasive about watching a possibility turn into software before the weekend ran out.

The event provides a smaller, more tangible picture of her interests than a mission statement does. People had technical skills. They had an issue they wanted to address. Someone created the conditions for them to work together. A finished game made the argument for their abilities considerably more efficiently than a panel discussing whether they possessed any.

Jackson was learning from founders while encouraging them. She had experience assessing companies and financing plans; they were building products in a changing technology market. Her move into entrepreneurship put her own assumptions to work in public. Advising someone to take a risk is easier when your own name is not on the business. She chose to put hers there.

First, make the ask easier

The early Plum Alley helped women sell products and raise money through crowdfunding. By 2013, its offering included access to experts alongside fundraising. This version of the business dealt with the first, frequently untidy stage of financing: a creator needs a budget, a convincing description and enough supporters to get moving.

Jackson’s advice was practical. Uploading a campaign would not summon a crowd of generous strangers. Founders needed to organize their networks, identify potential contributors and ask. The platform offered guidance on the mechanics, from shaping a campaign to presenting the project. She understood that a person could be very good at making something and still need help making the case for it.

That attention to process is easy to overlook in a career about access. Access has administrative details. A vague instruction to seek funding leaves a founder with the same blank screen. Instructions, feedback and a way to reach supporters give the next step a shape. The early platform tried to make a difficult task less mysterious, one campaign at a time.

A dinner-table measure of progress

As Plum Alley developed its investment business, Andrea Turner Moffitt became a central collaborator. Their membership approach brought investors together around private companies. Jackson had noticed a difference between the dinners she attended in her Wall Street years and dinners with her female friends. At the former, new businesses and investment opportunities came up naturally. At the latter, those conversations were largely absent.

In 2022 she described a memorable reversal: arriving at a dinner with female friends and hearing them discuss founders’ strengths and weaknesses, and the companies Plum Alley had introduced. The conversation had changed. They had something concrete to assess together. For Jackson, this was a career highlight, an unusually domestic measure of progress in a field fond of announcing milestones with dollar signs.

The anecdote explains an ambition that a portfolio list cannot quite capture. She wanted people to participate in choosing what gets built. An investor who can discuss a founder’s decisions has moved beyond the position of spectator. The dinner mattered because the women were forming judgments of their own. There was room for enthusiasm, disagreement and another question before anyone wrote a check.

The banker brings her own table

Jackson’s continuing ties to Columbia connect the different phases of her career. She has advised on entrepreneurship, supported the university and judged startup competitions. In 2018, Columbia recognized her contributions with its Coaching Columbia award. These are places where a former banker’s accumulated experience becomes useful to someone still working out a first pitch.

Recognition also arrived outside the university. Fast Company included her in its League of Extraordinary Women in 2012. Bpeace honored her with its Leader of Economic Impact award in 2016. In 2021, she appeared on Forbes’ 50 Over 50 list for investing. The dates make an appealing pattern: much of the public recognition followed the career she began after the one from which she had supposedly retired.

At a Goldman Sachs conversation published in 2018, she appeared alongside Davida Herzl, co-founder of the environmental intelligence company Aclima. The setting brought her career back to its starting institution, with a different subject on the agenda: expanding opportunity for women entrepreneurs. She argued for diverse perspectives in business decisions, including the straightforward value of having women involved when women are customers.

A larger structure for the same question

The firm now gives investors routes through funds and member syndicates. Its first venture fund lists Jackson and Avantika Daing as general partners. Its 2024 introduction of Plum Alley Ventures Company extended the platform toward funds organized around sectors and investment stages, with managers bringing expertise in particular domains. The structure has changed as the work has expanded.

The current team page gives Jackson three descriptors: optimist, learner and visionary. The middle word may be the most useful. She sought independence and work that would keep teaching her, and she has moved through institutions large and small while continuing to build them. There is a consistent curiosity underneath the changes in title.

Her story returns to a fairly ordinary scene: people sitting together, discussing whether a founder can make an idea work. Jackson has spent years trying to change who gets to join that conversation and whose company earns a hearing. The failed retirement supplied more time for the task. It also gave her a good line. Even bankers appreciate an unexpected return.