21 Lessons I Learned Starting a Business at 21: Part I
By Kathryn Cross
At the onset of these “unprecedented times,” I was sent home to graduate from Wellesley College from my home and await the delayed start date of my job. Because reading and TikTok dancing can only occupy so much of my lockdown days, I began considering different business ideas, wondering how I could use my newfound time to be productive and make some sort of positive societal impact. Knowing that the economy was experiencing a downturn, small businesses were struggling, and many students were left with jobs who were delayed or rescinded, I had the idea to start a management and marketing consultancy for small businesses. I wanted to instill a Gen Z, digital native mentality into clients that were struggling to digitize and empathize with younger consumers and apply my own financial services and management consulting experiences knowledge to pricing, hiring, and other obstacles.
“Call it ‘Bridge Strategy,’” my best friend said one morning when I told him about my idea. “That way, it will bridge the generational gap.
With a name in mind, I began coding our website on a Thursday in June. I spent all of that Friday strategizing how to reach out to consultants, emailing my school’s prominent Google groups and posting on my own social media. By the end of Friday, I had almost 20 people interested (many of them had summer internships cancelled). On Saturday, I would acquire clients, and that coming Sunday, I organized a Zoom with my 20 new consultants and began assigning them projects.
Through relentless Facebook messaging on alumna groups, I acquired 4 clients for what I wanted to be our very first “cohort.” Using Excel and promoting the idea that people can be staffed on the projects they want, I conducted my call for where I wanted the company to go on Sunday, ending my project-filled weekend by creating WhatsApp groups to coordinate projects.
And we were off, thus initiating the most formative, educational experience of my life, where I learned the following lessons:
Women are more cautious about speaking up and interrupting one another.
As a Wellesley alumna, most of my clients and consultants were also from historically women’s colleges; I only had three men as consultants at the start of Bridge Strategy: my friend’s little brother, my high school best friend, and a Wellesley consultant’s high school friend. Consequently, most teams were women with one man or all women. While I had already observed in my classes at Wellesley that women tend to be more cautious when speaking, it was even more fascinating to view this socialized behavior in real time in a corporate environment. When the teams were all women, many were cautious to speak, not wanting to step on the toes of the other consultants and always allowing others to speak before them if they spoke at the same time. However, when the teams were mostly women, I found that, while the men tried to make space for others to speak, they were not afraid to boldly state their own opinions either. However, my sample size of male consultants was small, and my observations were certainly generalizations.
It’s important to have emotional intelligence when you’re client-facing.
Especially in a client-facing business, emotional intelligence can be more important than analytical skills. For instance, the Bridge Strategy project leaders frequently had a very high EQ, and I felt as though I could trust them with client meetings even if they had never met them before and knew very little about the client.
Meeting content should include only the information relevant to those in the meeting.
It’s important that consultants are aware of what should specifically be discussed during meetings — especially with clients. Likewise, it’s important to keep internal housekeeping matters/general negotiations that do not pertain to consultants outside of meetings with the entire team and the client.
Always be transparent.
Throughout college, if I was ever uninterested in an extracurricular project, I always felt too guilty to speak up about it, leading me to contribute less than I normally would. Similarly, if I could no longer commit to something, I always felt bad about letting someone know, especially if I committed recently. However, as a leader of an operation, I realized that if someone was uninterested or losing steam in any way, I would rather have someone be immediately transparent with me than suffer in silence. An honest, official review of a consultant’s desire to engage is far more preferable than an opaque one. And, if the best outcome is to part ways and move on, then so be it, with no hard feelings.
Being a student offers invaluable resources.
I started Bridge Strategy one month after my graduation from Wellesley. Because of this, I was still able to utilize the technology and resources I had used in college. Having access to a Zoom that offered unlimited meeting times, summer internship stipends (thankfully with flexible deadlines), Facebook groups/Google groups, and more became extremely helpful when it came time to staff my business.
Always ask yourself, what would a man do?
At one point, I spoke with quite a few Wellesley alumnae entrepreneurs and experienced investors concerning how to go about compensating myself and the consultants for the services that we offered. I wasn’t sure how I wanted to approach compensating myself or even soliciting pricing. It almost felt like I was taking up too much space by giving myself too much and/or asking for too much. One Wellesley entrepreneur paused after I explained my options to her. “What would a man do?” she said.
Entrepreneurship is simply “winging it.”
When I was initially reforming our business model after acquiring a couple of clients, I asked one of our very first clients’ founders for advice. I told her that, as I was transitioning the business model, I felt like I was really winging it on the spot frequently. “If you told me that you weren’t winging it, I’d be concerned,” she said.
If you’re met with little resistance, it’s what you’re meant to be doing. However, resistance can also be good for business because it causes you to reevaluate.
This same former client of Bridge Strategy’s also thought it was fantastic that I was able to procure so many clients and consultants so quickly.
“At a certain point, I stopped recruiting both. There was an entire two weeks where new consultants and clients were all referrals from other people,” I told her.
“If you’re met with little resistance, I think it’s what you’re meant to be doing,” she reassured me.
However, I have also seen that some resistance (for instance, having too few clients) additionally made me reevaluate my previous tactics and try to be creative with my future endeavors.
Legal work is very real for entrepreneurs.
At the beginning of Bridge Strategy’s operations, I very broadly defined our legal responsibilities, thinking that I would figure it out as we grew. However, at a certain point, I realized that it was actually quite easy to access proper contracts, turning to sites like LegalZoom and others that provide templates. So, approximately two months into Bridge Strategy’s work, I began drafting contracts, individualizing each of them to our clients’ needs. While our first client to sign the contract was quite easygoing and had no alternative requests, as I drafted more contracts, more clients had addendums — one client even had nine. I was surprised at how varied clients’ reactions to certain contracts were as their needs and foreseeable plans were quite diverse.
I also realized that — when it comes to legal negotiation — it is acceptable to additionally push back on some asks, ensuring that both parties can come to a proper agreement. In some of my first client negotiations, I did take some legal revisions personally, seeing some of the requests as unfair to my own business and/or legal experience and plans. However, in all honesty, it really is just the course of business for both parties to engage in legal negotiations beneficial to their viewpoint.
Unpaid internships are a means of advancing existing privilege and oppressing marginalized groups.
Bridge Strategy’s first few clients were pro bono as I thought we could help businesses with the most need and acquire clients easily even with very little experience as a firm. However, as I observed people like Alexandria Ocasio-Cortez being praised for mandating that all of her interns be paid higher than other Congressional interns, I began to consider the implications of unpaid work.
Because I was continuing to model on the side, there were times when I was offered unpaid opportunities for high budget productions. While these gigs can be beneficial as they offer exposure to the entertainment industry and being on set as a whole, I soon realized that high budget productions offering unpaid work additionally came with less value placed on my on-set work conditions and the production as a whole. So, I began to reflect deeply on the value of unpaid labor and its intersectional ramifications in relation to gender, race, and income inequality.
When we were still operating as a pro bono firm, I tried to find grants that would be able to cover the cost of a salary from each of our consultants’ schools. However, private institutions’ deadlines for grants had passed and public institutions did not have ample grant money for these kinds of projects. Luckily, I was able to get Wellesley to supply a small stipend to their students, but other schools had no luck. With Bridge Strategy now operating on longer project timelines with paid clients, I feel more confident in promoting opportunities.
Stay tuned for Part II!
Want to learn more about Bridge Strategy? Check out their website, and follow them on social media:
LinkedIn: https://www.linkedin.com/company/bridge-strategy
Instagram: @bridge.strategy
Facebook: @bridgestrategypartners
Meet the Writer
Kathryn Cross is a Wellesley College graduate who is currently working as the Managing Director of her Gen Z-oriented management and marketing consultancy, Bridge Strategy, and as a UX/Product Designer at Publicis Sapient. In her free time, she co-hosts a fashion and pop culture podcast, Statement Piece, and models.
