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21 Lessons I Learned Starting a Business at 21: Part II

21 Lessons I Learned Starting a Business at 21: Part II

By Kathryn Cross


Missed lessons 1-10? Check out Kathryn’s first article here!

11. People are more inclined to try new things if there are no barriers to entry.

When Bridge Strategy’s work was pro bono and consultants had to sign up for projects on a client-by-client, volunteer basis, people were very willing to sign up for more than one project, large projects, projects in different industries, and more. Once I started taking on paid projects, due to the fact I wanted to be able to compensate consultants reasonably, I knew I had to limit the number of consultants per project. I would be interviewing consultants to staff projects accordingly.  Some consultants reached out asking whether or not I thought they would be qualified for certain projects and expressed uncertainty about their abilities. Having a consultancy of mostly women and only a few men (none of whom hesitated to be a part of certain projects), I immediately thought of the Hewlett Packard internal report that states that, “men apply for a job when they meet only 60% of the qualifications, but women apply only if they meet 100% of them.” As a result, whenever a consultant approached me with hesitation, I pointed out their strengths as a worker, consultant, and friend, emphasizing that, despite their own personal perception of their own work, they were indeed qualified.  

12. You don’t have to have a revolutionary tech idea to be an entrepreneur.

Throughout college, I always cross-registered into MIT entrepreneurship courses at the Sloan School of Management, racking my brain, trying to think about what could be the next big tech idea that would be worthy of a grant from its many venture-starting programs. Although my own tech experience is modest, I tried to be innovative, deepening my knowledge in areas that I had a particular interest in, such as fertility, women’s reproductive rights, and fashion, and how emerging technology could solve a pain point in those areas. Because Bridge Strategy was not a tech company, when I started Bridge Strategy, I essentially saw it as an extension of my college club experience. But, after we surpassed around 12 clients and students were reaching out to me through LinkedIn looking to join, I began considering the idea of adding “entrepreneur” to my list of personal adjectives. At the onset, I felt a twinge of imposter syndrome, questioning whether or not my small project deemed me an entrepreneur since consulting is an age-old business model. However, once I certified Bridge Strategy as a C-Corp, I realized that I was indeed an entrepreneur and that even consulting — a business model that has been done time and time again — is indeed a legitimate business model. My first business was not the glass ceiling-shattering, groundbreaking tech idea that I thought it would be, but it was my business nonetheless.

13. Bonding can be crucial to a workplace.

Once Bridge Strategy began acquiring an increasing number of paid clients, some consultants inquired about bonding activities. As project timelines were lengthening, they wanted to get to know one another, network, and utilize the amazing resources that came about within our fruitful group of consultants. So, two and a half months in, I created a Facebook group for all of our past and present consultants, encouraging them to get to know one another within the group. Additionally, I organized bonding events for each of the groups, even utilizing fun games like “Never Have I Ever.” At the end of the day, I think it made us friends as opposed to simply a corporate team, making us all more empathetic to those who needed to take a week off due to family matters or those who had questions or concerns about our ongoing projects.


14. If you own a business, take ownership of it.

About five weeks into operation, word of mouth and my own social media posts had knowledge on Bridge Strategy, ultimately bringing us to the milestone of onboarding people who were even older than I am. Immediately assuming that older people would automatically be wiser with their business decisions and have more work experience, I made the unprecedented move of allowing our first older onboarded person to be a project leader on their first project (prior to this, I generally recommended that people train as consultants on at least one project beforehand). I quickly realized that she was not the right fit for our culture, ultimately deciding that it would be best if I asked her to leave soon after she joined. Because she had been a part of Bridge Strategy for such a short time, I was hesitant, feeling guilty for asking her to leave so abruptly. However, after speaking with many mentors and other consultants who worked with her, I realized that I built Bridge Strategy from the ground up, and I had thus earned the right to make executive decisions as such. 


15. As a leader, it’s okay to have others advise your decisions, but it’s important to spread your own wings to invest in and maintain your own culture and vision.

When I first began managing Bridge Strategy, I almost always asked two of my most knowledgeable, practical, and thoughtful friends for help at every step of the way, inquiring what they think made the most sense. There were times when I felt like I had nothing together. My mind felt scattered, and I had so much to do: consultants to assign to projects to, clients to reach out to, deliverable presentations to attend, onboarding interviews to conduct, marketing materials to compile, and a website to update.  

“My little brother thinks that Bridge Strategy is running like a well-oiled machine though,” my friend told me (they were both working for Bridge Strategy at the time). I felt so thankful for those who let me lean on them, but at a certain point, I knew it wasn’t their responsibility to always make me feel secure. I had to spread my own wings, be confident in my decisions, and believe in what I had created.


16. There’s an immense business model difference between selling a product and offering a service.

I always thought that regardless of the offering, a business would run in pretty much the same fashion. However, as I began running this operation that was solely offering services, I realized that there is an immense difference between offering a product and a service. Products are standardized and every time you give a product to a consumer, they receive the same product. Product-facing entrepreneurs may always be conscious of consumer feedback and have to tweak this product, releasing updates, and/or keeping up with trends. Service-facing entrepreneurs have to create clear guidelines for what they are offering and they have to plan out a whole new product every time they are offering one — as I was.  


17. Always follow up.

When networking, it’s important to always follow up with anyone even minutely involved in any interaction. It’s how you sustain relationships and others’ investment in yourself. Similarly, when taking on job opportunities, it is important to always follow up. When consultants asked me about what the time commitment looked like for Bridge Strategy, I always told them that the only thing that I asked was that they be transparent with their abilities to commit and follow up if they ever think they will be unable to meet these expectations. I most appreciated when people were up front about not being able to be as committed as they had initially thought. Those who were prompt, responsive, and continued communication were the people who had the most respect from others, I’ve observed.


18. People don’t always voice their opinions. The best leaders ask and listen.

Because I love public speaking and Wellesley taught me that women should be outspoken, I try to be as public as I can about my own opinions. So, when I first started Bridge Strategy, I always assumed that consultants would volunteer their own thoughts on how we can be a more efficient consultancy. However, I soon realized that many held off on expressing their opinions, only volunteering them when I created a space for them. When our first two-week sprint (we called them a “cohort”) ended, I asked some consultants who had to drop off due to other commitments if Bridge Strategy could be improved in any way. To my surprise, many had a lot of great suggestions that, otherwise, would have gone unheard. For instance, at the beginning, many mentioned networking/bonding opportunities could be more prevalent and help build more of a sense of community (as a result, I created a Facebook page where consultants could network and suggested bonding activities at every project kickoff; ultimately, this even led to some consultants getting internships through others at Bridge Strategy).  This proved to me that a good leader not only takes space, but can also make space, specifically for others. The best leaders are the best listeners, after all.


19. As an entrepreneur, you truly do wear many hats, but, it’s okay to let others wear hats, too.

When I was trying to get Bridge Strategy off the ground, I was trying to figure out front-end web development, legal work, pricing, and more. But, I never asked others to take on these tasks because I assumed that they would mainly be interested in consulting, the essence of Bridge Strategy, as opposed to its growth and future. I was not sure if anyone would want to take on the investment that comes with wearing many hats.

Thankfully, there was one Wellesley alumna who offered to be head of internal strategy because she mentioned that she enjoyed doing more operations-related tasks. I was so grateful for her work because it taught me that other passionate people could invest in my business and want to see it grow as much as I did. I did not have to be the only one wearing so many hats because any new startup requires a village, and a village is made of more than just one passionate contributor. Creating this formalized operations managerial position was one of the best things I could have done for my business, allowing myself to give some of my hats to someone, relinquish some control, and better understand trust within business.


20. Separate business from personal.

As previously mentioned, there were friends I leaned on at the beginning of Bridge Strategy for advice and encouragement. However, as Bridge Strategy began to increasingly occupy these normally personal conversations, I realized that I was not investing in my friendships in the same way that my very kind, loyal friends were investing in me and my business. My business’s growth and future was just always on my mind. This infringed on my personal life as a result, occupying conversations that I was having with friends who were not even involved in my business. I saw that it is important to draw boundaries between business and personal, as I could not be a good friend if I was constantly worrying about myself and my own business. 

21. You can always learn from others.

Finally, because Bridge Strategy began as a passion project, I am so grateful for all of the consultants, operations managers, friends, mentors, and more who gave me confidence that it could be a business and that I could be an entrepreneur. The clients we had helped uplift my own personal entrepreneurial abilities as well. So many of our clients were one-woman shows who were single-handedly offering sustainable products, being featured in Vogue, enhancing awareness around COVID-19 precautions, and so much more. Clients have also always presented us with unique pain points, teaching me invaluable management and marketing consulting skills, including how to craft an effective e-mail marketing campaign, redesign user and web interfaces, assess pricing models, and reconfigure costs to make an additional hire. Having acquired our 27th client this past week, I hope that Bridge Strategy will only continue to grow small businesses, and concurrently, help students feel as though they can unequivocally contribute to business growth. At the end of the day, the consultants who tell me that they have had an educational experience at Bridge Strategy or who spoke about Bridge Strategy during an interview for a job that they got is what motivates me. These words of encouragement always keep me going. 


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



Kathryn Cross headshot.jpg

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.





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