Barry O’Reilly welcomes Shiyan Koh as this week’s guest on the Unlearn Podcast. Shiyan is Managing Partner at Hustle Fund, a VC fund that invests in pre-seed software startups in the US, Canada, and Southeast Asia. Often, they write the first check or are in the first round of funding. What makes Hustle Funding different is that, beyond the usual criteria that VCs look for, they tend to prioritize founders that have speed of execution. In today’s show, Shiyan and Barry discuss her professional experience, from her beginnings in finance to her current role at Hustle Fund.

A Whole New World

“I’ve never been one for ten year plans, so I cannot tell you that [I knew] I was going to end up here,” Shiyan tells Barry. She hopped from one opportunity to the next, thinking about what she was going to learn and who she was going to work with. One major interest was policy creation and regulation, which she defines as “systems being enacted on people,” so she surprised herself when she delved into investment banking after receiving an internship in college. “I didn’t really know what I was showing up for, but opened up a whole new world,” she says. The company that offered her the internship, JPMorgan, invited her to work for them as a full-time employee, which she accepted. Eventually, however, she decided that the job and the industry weren’t in her long-term game plan. [Listen from 1:46]



Finance, to Growth Stage Venture Capital

“Nothing sharpens people’s behaviors more than money,” Barry comments. Shiyan talks about how she transitioned from investment banking, and how that experience helped her determine what to do next. “I thought [to myself], ‘I don’t want to be an investment banker anymore, but let me reflect on the things I enjoyed about the job.’ [So I] made lists… When I thought about all the different projects I’ve gotten to work on over the course of my time there, I realized that my favorite ones were the young companies, the ones who were just going public. And so I went ‘You know what, I want to do more of that.’” [Listen from 7:43]

Growing Beyond Growth

It’s much easier to model growth in an Excel sheet than it is to make it happen. Shiyan recalls what she learned from her stint in growth stage venture capital. “I often felt like a fraud in those board meetings because I had never sold anything in my life… there was a huge gap between theory and practice.” Emboldened by her lack of knowledge, Shiyan resolved to attend business school to grasp a better understanding of how to build and run a business. Yet once again, she determined that this wasn’t what she wanted to do. Just because something is intellectually interesting to you, it doesn’t necessarily mean it’s a good job for you, she affirms. [Listen from 11:08]

NerdWallet and Takeaways

Shiyan dives into her time at NerdWallet, where she was VP of Business Operations and Corporate Development. Incidentally, the founder of NerdWallet was a friend of hers. They were together for a casual meetup when she asked him if he knew of any interesting companies in New York, to which he replied with an offer to join his company. She goes on to describe her experience commuting from New York to San Francisco every few weeks, which culminated in getting a second apartment per her mother’s request. “The big takeaway from startups is that only 2 of the 100 things to do on your list are existential; you just need to let 98 things burn until they [reach that level],” Shiyan advises listeners. “You just have to focus on existing topics.” [Listen from 19:58]

Alignment and Action

“One thing I personally struggle with is finding the balance between the appropriate amount of time to invest into getting people aligned with what you’re trying to do, and getting them to take action,” Barry shares. If you spend too much time on alignment, no action will take place, and vice versa. One thing that’s hard for a lot of people to imagine is that startups move so fast, and as human beings, we’re unaccustomed to that rate of change, according to Shiyan. We develop routines for control, but when things shift too quickly, we become stressed and emotional. You then have to investigate ways to help people continue to be productive and high-performing. [Listen from 30:08]

Listen to the previous episode with Dr. Erik Reis on How Maximizing Your Brain Can Maximize Your Business
You may also read my recent blog on Facing Your Fears And Unleash Your Potential