Kristen Craft is a proven entrepreneur with more than 15 years of experience in enterprise software and digital marketing. In her role as director of early-stage startups at Silicon Valley Bank, she’s become known around the Boston startup community for her passionate support of founders.
Craft has helped build several prominent brands in Boston and is committed to supporting companies with excellent cultures and strong values. Her past experience includes leadership roles at Animalz, Tettra, Ovia Health Wistia, and Transparent Language, as well as launching her own startup Brown Box Storage.
A lifelong learner, Craft earned her bachelor’s from Brown University and a master’s of education at the Harvard Graduate School of Education. Upon graduation, Craft decided she wasn’t ready to leave the classroom just yet, so she went on to MIT’s Sloan School of Management to earn her MBA.
In this episode, Craft discusses the various challenges entrepreneurs face when first building startups (and how you can avoid them) and the importance of following the proper steps when starting a business. We also explore her Harvard, Massachusetts, roots, her early jobs as a teenager and our mutual passion for reading with our children.
You can listen to our podcast discussion embedded below or on any podcast platform you prefer (SoundCloud, Spotify, Apple Podcasts, Stitcher, and Google Play):
Where did you grow up? How would you describe your childhood?
I grew up an hour outside Boston in Harvard. My father was an immigrant and entrepreneur, and my mother built her career as a city planner and at Bank of Boston focused on fair lending. Growing up in the middle of the woods, my childhood mostly revolved around reading and exploring outside.
Who were your role models growing up?
I always loved the rebels! I liked actors like Drew Barrymore who broke the rules a bit.
What is one of the biggest lessons you learned from your parents?
Both of my parents were bullish on school and hard work. I think they helped me build strong habits from an early age.
Did you always love learning? Were you always a good student? Even in your younger years?
I have always loved learning and reading and trying new things. I generally did well with grades and on tests, but I also got in trouble for chatting with my friends or tree climbing too high during recess.
What is the first career you remember wanting to pursue?
My father was a shoeshine boy when he was growing up, so I decided I wanted to be a shoeshine as well! I didn’t end up doing that, but maybe someday. For a long time during my teenage years I wanted to be a teacher.
What do you love most about helping startups grow?
I love the mixture of strategy and people. On the strategy side, I find it really fun to think through how to deploy capital for growth or how to position and market a product. On the people side, I do a lot of mentorship in my spare time. I love helping mentees and founders alike think about how they can lean into the strengths or zones of genius! (Feel free to ask me about this…it’s one of my favorite topics!)
What characteristics of a founder do you find to be the biggest differentiating factor for those who succeed vs. fail?
In the early days, I think it’s all about openness. I really admire founders who are open to new ideas, new perspectives, new people. This needs to be paired with strong opinions and conviction as well, of course.
According to the Small Business Administration’s Office of Advocacy, roughly 80% of small businesses survive the first year. Only about half of small businesses survive past the five-year mark. Only about one in three small businesses get to the 10-year mark and live to tell the tale. What are the most important characteristics of those who make it to that 10-year mark?
Grit. There are so many ups and downs for most founders, and grit and hustle usually help you accelerate and build on your wins on a good day and stick with things on a bad day. “Elbow grease” (as my mother would say) goes an incredibly long way.
As a senior level director and startup advisor/investor, do you have any advice for young people that are seeking a similar career journey? Where should they start?
Try to gain as many experiences and perspectives as you can. Try starting a small business. Try angel investing. These kinds of small bets can help you start to pattern match what you’re good at and where your energy lies.
As an investor, what qualities do you look for in a company’s culture before you decide to step in as an advisor or investor?
A smart idea with a clear path to revenue and a clear perspective on growth strategy. I came up through bootstrapped companies vs. VC backed (mostly), so I have a bias towards profitability.
Reflecting back to your earlier year starting out, is there anything you wish you had done differently to get to the point where you are today?
I wish I’d come into the office five days a week from day one (vs. the three days/week I did when starting out). I love the energy of downtown Boston, and we have an incredibly smart, talented team here at SVB. I’m a big believer in the value of ad hoc brainstorming and creativity. I suspect I could have ramped even faster had I been with our team in person every day.
Is there a particular person or event that helped shape the career path you took?
My boss and hiring manager Jesse Bardo. He saw how much I love working with startups and love our community. He’s also one of the most bullish people I know when it comes to DEI. We originally met because he was so adamant about making sure there was better female representation at an angel investor event he hosted. If it weren’t for him, I wouldn’t be here at SVB. I admire him tremendously and feel so fortunate to get to work together.
What is the biggest challenge you’ve overcome getting to where you are today?
Honestly, I think I’ve created my own biggest challenges. Specifically, I think there have been moments in my career when I pursued something I believed I was supposed to pursue or supposed to want….even if it didn’t really align with what I enjoyed. My biggest regrets and frustrations are with decisions I made about myself and my career path. I wish I’d been better able to block out my own ego and/or beliefs about what I should do.
How would you describe your style of work compared to others in the industry?
My style of work is extremely collaborative. I derive the most energy and am most motivated by those around me — ie., I want to do right by our startup clients and I want to do right by my team. Luckily, nearly everyone at SVB operates in this way, which makes for a terrific culture. It also means that our goals and incentives are extremely well-aligned with our clients’ goals.
On a more macro level, I believe in the “rule of seven” — ie., most people need to engage with a brand or product seven times before remembering it and/or taking action. I keep this top of mind in how I work within our New England startup community. I see other banks spending money on billboards but doing little work on the ground in support of startups. I don’t see this as a winning formula. Instead, I believe in showing up day in and day out, putting in the “elbow grease” of helping our founders grow, and building community. This kind of real commitment to our startup ecosystem is what will drive long term success for our local founders and long term success for SVB’s reputation as the best of the best.
What sorts of challenges and opportunities have you found in the pivot to virtual business and networking during the Covid-19 pandemic? How has the pivot “back to normalcy” affected you and your work?
Going virtual did a lot for the startup ecosystem. It became easier than ever to hire top talent because, all of a sudden, you could hire from anywhere. It also made it easier to fundraise, since VCs who previously preferred in-person meetings were willing to meet over Zoom.
We like the idea of ending our episodes with a challenge for the listeners/readers. Whether it be reaching out to an old friend, reading 5 pages a day from a book, creating a new healthy habit… what is one challenge you have for the listeners?
Try to pay it forward at least once per month. So many of us have benefitted from the generosity of past mentors, or on a more basic level, from someone willing to do an informational interview about their own career path. Even when my week feels busy and chaotic, I try to say yes to as many asks from those who are earlier in their careers. I’m likely not yet at once/week myself, but maybe voicing this challenge here and now will be the catalyst that I need as well to commit to this every single week!
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