Apr 7, 2017 · 27m · 20vc
20VC: How To Create FOMO For Investors, How To Manage VC Conversations & A Repeatable Process For Learning New Things with Anna Shedletsky, Founder & CEO @ Instrumental.ai
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings interviews Anna Shedletsky, Founder and CEO of Instrumental, about transitioning from Apple Watch product design to founding a hardware AI startup. Shedletsky shares actionable frameworks for founder domain mastery, candidate screening, engineering task prioritization, and strategic fundraising.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 30.3% of the talking time here. How this is scored →
Harry as informed peer 3.2 Guest teaching 4.6 Guest disagreement 1.2 Harry pushing back 2.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 16:50 Rejection of standard fundraising dogma
Anna rejects the conventional wisdom that founders need an existing term sheet to create fundraising FOMO, outlining a creative work-around using YC interview deadlines.
Hardest push from Harry ▶ 11:27 Harry questions culture screen diversity impactHarry directly challenges Anna's hiring screen based on conversational rapport, noting it can easily produce a homogenous team devoid of diverse perspectives.
Biggest teaching moment ▶ 8:30 Anna's systematic framework for rapid skill acquisitionAnna takes Harry through a thorough 5-step process for rapid learning and skill development, providing actionable tactical advice on how mechanical engineers master software hiring.
Harry holds his own ▶ 11:27 Harry identifies cultural diversity trapHarry demonstrates keen organizational insight by pointing out how subjective rapport-based interview screens inadvertently stifle diversity.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Anna's Background & The Genesis of Instrumental | 2 | 3 | 1 | 1 | Harry welcomes Anna and asks standard background questions about her transition from Apple to founding Instrumental. Anna explains the difference between building one prototype and mass-producing millions of units, setting up the problem Instrumental solves. | |
| Key Takeaways & Cultural Values from Apple | 2 | 6 | 1 | 2 | Anna lays out Apple core values and walks Harry through her structured 5-step methodology for learning new disciplines. Harry assumes the role of an eager learner, making light self-deprecating remarks about being a new VC. | |
| Culture Screening and Diversity | 4 | 5 | 2 | 4 | Harry challenges Anna's culture screening process, pointing out that 'likability' filters can create team homogeneity and reduce diversity. Anna reframes culture screening as a search for passion, then explains how hardware engineers approach software stack-ranking. | |
| Unconventional Fundraising & Creating FOMO | 5 | 5 | 1 | 2 | Anna explains how she engineered fundraising FOMO using a Y Combinator interview deadline, bypassing the usual chicken-and-egg term sheet dilemma. Harry validates her strategy using his own perspective as an active venture capitalist. | |
| Managing Fundraising Risks & Pulled Term Sheets | 3 | 4 | 1 | 1 | Anna cautions founders against closing off investor discussions early due to the risk of pulled term sheets. The segment finishes with a lighthearted quick-fire round on CEO challenges, Tolkien, and unloved industrial software. |
Statements from this episode (12)
Shedletsky: US will permanently fall behind without manufacturing automation
“If we don't automate, others will, and we won't be able to catch up, and I think it's important to keep that playing field as level as possible for as long as possible.”
Shedletsky: Ask experts to evaluate each other's advice to resolve conflicts
“I especially like to collect advice from several people and then ask those people to give me advice on the advice I've gotten from other people, which is particularly useful when you're not really sure how to judge differing perspectives.”
Shedletsky: Filter candidates faster with a 15-minute upfront culture screen
“We actually found out it was easier and faster to figure out if someone was a fit by doing a culture screen first. It took 15 minutes and essentially it's, would I want to have a conversation with this person again after this call, or am I happy this call is o…”
Shedletsky: Founders must run parallel Plan B strategies for critical milestones
“Anything that's company critical, like Hiring this first hire or fundraising or whatever. You need to have a plan B”
Shedletsky: Instrumental screens job candidates for passion over uniform backgrounds
“I think Instrumental has ended up being a team of very kind of angular people, but we're angular in different ways, and ultimately, our screen is for passion, and so we ask candidates to tell us about something they're passionate about, and that could be work-…”
Shedletsky: Instrumental generated investor FOMO using a Y Combinator interview date
“A few months after taking angel funding, we applied to Y Combinator, fully intending to try to get in because we thought it would be a great network for our company, and our application was selected for an in-person interview, and I picked a date three weeks o…”
Shedletsky: Asking VCs for advice yields free consulting and builds relationships
“I think what I have kind of stumbled into is you just go and ask advice. This is a great way to get like half an hour of free consulting about what you should be worried about in your business and what you should be doing about X, Y, Z, or the other.”
Stebbings: VCs view founder referrals as the highest quality introductions
“There's also no better referral than a founder referral for VCs. They take that as kind of the highest form of solicitation.”
Shedletsky: Instrumental had a high-watermark term sheet pulled during redlines
“We had our high watermark term sheet pulled on us for what we believe was no fault of our own. A week after we thought we'd finished the pre-signing due diligence and had Started trading red lines back and forth, and that pulled term sheet created difficulties…”
Shedletsky: Founders should secure at least two term sheets in parallel
“The best defense seems to be to have at least Two high watermark term sheets that you can work with in parallel, and to kind of not close down conversations just because you think you're done, and you just really want to be done with the fundraising process.”
Shedletsky: Machine learning's biggest manufacturing opportunity is full-line feedback control
“I think what's most exciting is what we're working on, which is creating closed loop feedback control around the manufacturing line, not just one specific process, as is kind of done today, but the entire line, the entire supply chain, and I think that's a sup…”
Shedletsky: Manufacturing lags in tech adoption due to focus on execution
“It's pretty antiquated, and the processes are pretty antiquated, and the people who work in this space are really always just focused on executing, and so they don't have a lot of time to think about how it could be better and what technologies could be better…”