Founder Track
Ready to connect with your peers in entrepreneurship? Grab your free ticket for Startup Boston Week on Sept 14 - 18 today!
Early-Stage Sessions
Persevere, Pivot, or Pull the Plug? How Founders Evaluate What Comes Next
Every founder eventually hits a crossroads: quit the stable job or keep the side hustle going? Push through slow traction or admit the market isn’t responding? Pivot the company, stay the course, raise more money, or shut it down entirely?
The problem is that most startup advice talks about these moments in hindsight - after the successful pivot, the big exit, or the inspirational LinkedIn post.
This session focuses on what these decisions actually feel like in real time, when the answer is messy, emotional, financially risky, and deeply uncertain.
You will walk away learning:
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The financial, personal, and business milestones founders should evaluate before going all in
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How to determine whether a startup has enough traction or signal to justify doubling down
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What metrics and customer behaviors matter most when evaluating pivots
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How to think about opportunity cost, risk, and regret during major startup decisions
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What signs may indicate it’s time to shut something down and how founders can do that responsibly
There’s no universal formula for knowing when to persevere versus move on. But hearing how other founders navigated these moments - honestly, imperfectly, and without survivorship-bias fluff - can make the decisions feel a little less isolating and a lot more informed.
The Earliest Team Decisions Hit Different: Co-Founders, Ownership, and Your First 10 Hires
Most founders spend a lot of time thinking about product, fundraising, and growth. Far fewer spend enough time thinking about the people decisions that quietly shape whether the company survives in the first place. Who you choose as a co-founder, how you divide ownership, and who you hire first will influence your culture, speed, communication, and ability to scale long before there’s an org chart or HR team to clean things up later.
This session explores how founders build the human foundation of their company from day zero through their first 10 hires.
You will walk away learning:
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What conversations co-founders should have before officially building together
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How founders can divide responsibilities, decision-making authority, and ownership early on
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How to think about equity when contributions, risk, or time commitments differ
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What roles founders should prioritize in their first 3–10 hires
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How to identify whether an early hire is truly built for startup environments
The earliest people decisions in a startup tend to compound over time, for better or worse.
Whether you’re still looking for a co-founder, formalizing your founding team, or preparing to hire your first employees, this session is designed to help founders make smarter, more intentional decisions before small problems become very expensive ones.
Solo Founder, Full Team Energy: How One Founder Can Build and Scale with AI
There’s a growing category of founders quietly building companies that look much bigger from the outside than they actually are. Customer support? Automated. Marketing? AI-assisted. Operations, research, product workflows, investor prep? Also increasingly handled through AI systems and smart automations.
Rather than talking about AI in vague future-tense hypotheticals, this conversation focuses on the reality of operating an AI-augmented company today.
You will walk away learning:
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What AI tools were most useful at different stages of growth
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How to build AI workflows across marketing, operations, product, research, and finance
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Where AI is genuinely “good enough” and where human expertise still matters
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What automations and systems compound into long-term operational leverage
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How solo founders can present themselves credibly to investors and customers
Building solo no longer has to mean building small. Whether you’re intentionally staying lean or simply trying to maximize runway before hiring, this session will give founders a much more practical understanding of how AI can extend their capabilities, without pretending it magically replaces an actual company overnight.
Your Startup Story Might Be the Problem: How to Pitch Clearly, Confidently, and Actually Get People to Care
A surprising number of founders lose the room before they ever get to the traction slide. Not because the company is bad, but because the story is confusing, too broad, overly technical, or impossible to emotionally connect to in the first few minutes. We’re breaking down how founders can craft a sharper, more compelling startup narrative and communicate it effectively in the moments that matter most: fundraising, hiring, customer conversations, and high-pressure pitches.
You will walk away learning:
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How to communicate the clearest, simplest version of your startup story
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What makes investors emotionally engage with a company quickly
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How your narrative should change depending on the audience
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How to project confidence without sounding robotic or overly rehearsed
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How to craft a stronger 30-second version of your company story
Founders spend a lot of time refining the product and not nearly enough refining how they talk about it.
Whether you’re fundraising for the first time or trying to understand why pitches aren’t converting into momentum, this session is designed to help founders become clearer, sharper, and significantly harder to ignore.
Meet Jill Kravetz! Jill is our Founder Track Lead for Startup Boston Week 2025. This is her first year on the Startup Boston Organizing Team.
Some fun facts about her: her go-to method for unwinding after a busy day of startup hustle is playing puzzles, specifically jigsaw and Sudoku. Look them up and connect with them on LinkedIn.