How I Started My First Consulting Business: Confessions of a Bain Consultant


This month’s Transparency Series article, How I Started My First Consulting Business: Confessions of a Bain Consultant, is all about Jenny Rae’s renegade life and her first business that wasn’t a souped-up lemonade stand.

If you haven’t read Part 1, Part 2 or Part 3 of our Transparency Series (on Jenny Rae’s journey before, during and after Bain), make sure you start there – it will illuminate the back story to what we share here. Enjoy!

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My dad and my little sister accompanied me from my home in Pennsylvania to the airport at BWI to launch my journey. Sure, I’d just returned from an around-the-world trip – and the U.S. was freshly at war – and I was about to fly out on a one-way ticket and embark on what turned out to be a life-defining journey…but I was dispassionate, ready to get on with it, ready to leave. I had a few thousand dollars to my name, a whole lot of get-up-and-go, and a bag full of idealism that fueled me on.

My dad, normally a stoic himself, cried as he hugged me and sent me away. He implored me to see the good in our family at home, in the U.S., and in George W. Bush as President (I recently found out my staunchly Republican dad had voted once for a Democratic candidate, and I almost had his mental stability reviewed because it was so out of character). I let him know that the world was my oyster, I had more important things to do than sit around and ride my bike to the farmer’s market, and I was out to make a dent.

I played it cool. But inside, I was terrified.

See, I’m this interesting breed of risk-taker. When I took flying lessons (stay tuned for the whole story a bit later on) I stopped after soloing because controlling a little flying piece of metal thousands of feet up in the sky scared the bejeezus out of me. I didn’t yearn to skydive, I don’t like to rock climb and I’ve never wanted to bungee jump. In short, I don’t take risks because I love them. I take them because I can’t stay where I am. I’m passionate but restless, frantic to disrupt the status quo, building my vision as I go.

So, I was terrified to leave and set out on my own. But I ultimately left the U.S. because I was even more terrified of becoming who someone else wanted me to be – of looking back on my life 5, 10 and 50 years down the road and not being able to say that I’d at least tried to follow my heart and do what I was born to do.

My brave and noble intentions were all well and good. The problem was, I just didn’t yet know what it was that I was meant to do.

When my plane landed in South Africa, it was winter. It’s amazing how the weather can affect the way you feel about a place. In the sunshine of summer, 6 months earlier, South Africa was glowing with a halo of possibility. When I landed in winter, the country seemed tied down, boxed in, closed up and unfriendly, and I immediately wondered if I’d made a huge mistake.

I had enough cash to last me 3 months, and I tried to spend it as slowly as possible. Fresh from backpacking training, I bought avocados, bread, Nutella, eggs and kept myself healthy while trying to establish some sort of routine.

And – I set out to get going, but going to what – of that I wasn’t quite sure.

I was fresh out of a formal work environment, where I worked by the hour and was told (at least generally) what to do – but now found myself in a place where I had to do my own thing. I found utter failure in an attempt to structure a day with no deadlines, no peer pressure, and no personal interaction. I certainly flunked my first week at least. I caught up with friends, hung out and planned to make plans… My computer stayed bolted shut and , in reality, I didn’t do a dang thing.

But it’s amazing how little choices can start to create shape from a blob of a life. In the darkness of winter, when I could have happily lamented my absurdity, made plans to return to the inevitable grind in the U.S., and defined myself by my inability to do something of grandeur, I started small. I set myself one target a day – write one story about my recent travels – and didn’t let myself leave the house until I did.

At the end of my second week, I had 3 good stories. Not every day was fruitful. Sometimes, what I wrote didn’t make sense. Sometimes, it just didn’t come together. Sometimes, it wasn’t interesting enough for anyone else to read.

But then, on the more magical of days, I wrote something that felt like a seed had been planted, and it grew and morphed until it was a story or a poem worthy of the light of day. I started to create. In the afternoons, I asked a friend to teach me to drive stick shift – I’m amazed to this day about how gracious he was to teach me.

At the end of my third week, I had shaped a vision for a book – my first book – outlining my travels around the world. I even wrote a dedication for it, and decided to offer the manuscript as the wedding present to my best friend, Lawson.

And all of a sudden, I had started something.

But while I’m a writer, I’m not just a writer; I needed to balance the solitude of creation with the dynamism of human interaction. So I took my faltering ability to drive a car on the left-hand side of the road, stick, up and down hills in Cape Town – and I began setting up meetings.

I started with a question – “Who should I meet because they are doing something amazing in South Africa?” – which eventually turned into a series of questions – “Who do you know who is passionate about corporate social responsibility? Who is doing something about racial reconciliation? Who is creating a business to drive economic change in South Africa?” And I started asking the question of everyone I knew, from a stranger in a coffee shop to a connection through my hometown in Pennsylvania, to members of my mixed-race church. And I began setting up lunches.

At the lunches, I began to dream out loud. Sure, I had no real marketable skills, but I had a freshman summer job where my defined role was simply to make a stock brokerage business better. Plus, I had taken a few classes in my day, and if my still-skimpy experiences (and my travels) had taught me anything it was that I could figure it out.

When one month was up, I had completed 3 lunches – one with a PR specialist who knew everyone there was to know, one with a published writer in her secluded beachfront cottage, and one in a fancy office for a financial services firm. For the second time (the first was from a mentor who worked for Coca-Cola in Washington, DC) I heard that Corporate Social Responsibility arms were where careers went to die – not hotbeds for radical social, political and economic change like I had dreamed. And I felt empty-handed.

Month 2 started, and I began to get worried. I was still writing, but my money was waning, and I wasn’t sure what to do next. It felt like I was eliminating options, but not coming up with a real way to make money. And then there was affirmative action and an excessively high unemployment rate – no-one really wanted to hire a woman fresh-out-of college with no tangible skills or experience to speak of.

I realized something that was consistent about all of the people I’d met with so far – they were all busy, and all needed help. So one day, on another lunch with another contact, instead of asking the man I was speaking with what they were doing and what they were passionate about, I asked what he wanted to do that they didn’t have the capacity for quite yet. Before I knew what had happened, I began to pepper him with questions – and I really sought to understand his pain points. 

In short, I asked better questions.

Why? Through the story I was weaving together, I realized that life wasn’t as pre-prescribed as I thought, and everyone leading an organization or a company didn’t operate from some mysterious locked-box master plan. When they came off the pedestal, I stopped focusing on how I could learn from what they had already done and began focusing on how I could meet their needs, and meet mine too.

For the first time in my life I really understood what a win-win really was.

Over the second month, I met with a communications writer, a publisher of a non-profit magazine for the homeless, the local Habitat for Humanity director, and friends of friends who were working for start-ups and tour companies. My conversations were more fruitful, my questions continued to push more, and I even laid out a few verbal proposals – sharing how I would help. The issues were clear, and they told me so – there were no formal jobs, and no budget for other potential issues.

I started to think that maybe one of my father’s sage pieces of advice – it takes having a job to get another one – was playing out.

On Sunday afternoons, I integrated myself into a family that had moved to South Africa because they wanted to. I’d never met a family like that before – they had built a business in the U.S., decided they wanted to raise their 5, eventually 6, children as non-traditional Americans with an actual global mindset and a heart to serve the poor, and seemed to be having a helluva lot of fun doing it.

I talked to everyone, but mostly to Aaron, the father of the clan and self-made businessman, about his philosophies and began to admire his processes. So, every Sunday afternoon, I joined in the madness – driving from the unique multiracial church I had started attending in a Township, or shack village, to their house or to the beach where they were hanging out – and back again for an evening gathering with friends in the swanky Southern Suburbs.

He regaled me of stories from a successful but complicated family business selling artistic frames to the building of a logistics business that he now ran 4 hours a week to the work he and his family hoped to do in South Africa. I also shared my issues and challenges with the “job search” and he told me to suck it up, figure it out, and make something happen. Hearing that from someone with a cushy job would have been hard, but he had grit and I needed a kick in the pants.

And in Month 3, I made it rain.

First, I finished the transcript of my book. Just shy of 50 short stories and poems, I chronicled my trip around the world – which I affectionately called my “Leap Year” – and its manic moments. This eventually became my book, Going Global. I wrote the dedication to Lawson and printed out the version to prepare it for layout. I also contracted a friend to compose darling illustrations.

Then, the month got sweeter via a meeting that my PR specialist networker set up for me. With whom? Mr. Butler’s Pizza, the founder of a Dominos-like chain with unique pizzas, that employed women from the townships to make the pizzas and college students from UCT to wear bowties and deliver them. And wouldn’t you know it? The research I had done in the bush in Ghana on malaria interested him in doing a project with me.

But looking back, with thousands of interview sessions between us now, I realize it wasn’t really my experience that sold him. Even more important than my history was how I handled the moment. I wasn’t merely asking for a job to make him solve a problem for me. I was spirited, confident, and bold enough to give him the assurance that I would make a mark on his company, even with little direction from him or other senior management.

I asked him about where he wanted to go, and he suggested that he was thinking of offering shares, bonuses, or even building houses for his staff and he wanted to know how to go about doing that. It was perfect. I set a price, I told him how I planned to gather firsthand data from his workers and assess programmatic options, and before I knew it I had my first consulting gig.

I was just hustling to make ends meet through meaningful partnerships and work. Of course, I didn’t know that that single project – and others that grew out of other conversations I’d had in my first month – meant I was knee-deep in the process of creating my first consulting firm. In fact, in a meeting at Lawson’s wedding the following month, I was about to find out that adding value is what consultants – real, top-tier consultants – do.

Without knowing what was coming, I boarded a plane for the U.S. with a consulting agreement in hand, the finished manuscript of Going Global: An Around The World Adventure, and a plan for a short bridesmaid break in the U.S. before I returned to South Africa to let the real work began.

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Stay tuned for next month’s Transparency Series article, Crashing Into Consulting: Confessions of a Bain Consultant, which talks about how I met the woman who showed me how consulting could further my passions and provide valuable training all in one.