How do you know if your idea is strong enough to build a company? When is the right time to raise funding, or hire your first employee? And what actually matters most at the seed stage?
In this episode of The Drafting Table, Jessica Lin, co-founder and general partner at Work-Bench, an early stage enterprise software & Saas VC firm in NYC, answers the most frequently asked questions from early-stage founders.From figuring out if you need a co-founder, to founder-led sales, to when to build a prototype, Jessica shares the unfiltered realities of startup life and why finding the fun might just be your biggest advantage.
Whether you’re pre-idea, pre-seed, or scaling your first customers, this episode is packed with battle-tested advice and frameworks to help you build with more clarity, confidence, and grit.
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⏱️ Timestamps
00:00 – Intro + Thank you for this Season
00:35 – How do I know if my idea is good enough?
01:56 – What does “venture scale” really mean?02:39 – How much traction do I need to raise VC?
04:32 – Should I build a prototype or MVP before fundraising?
05:34 – Do I need a co-founder? What to look for
07:46 – What do investors want to see at seed stage?
09:14 – How do I find and approach investors?
10:24 – How do I get my first 10 customers?
12:37 – How important is picking a specific vertical early on?
15:33 – How do I hire early employees without capital?
18:16 – What’s the hardest part of being a founder?
20:27 – How can I prep for being a founder before I make the leap?
22:13 – When should I hire a sales rep vs doing founder-led sales?
24:24 – What does product-market fit really feel like?
26:25 – Can I go enterprise-first? Or start with SMB?
30:33 – Why enterprise sales is all about change management
33:15 – 90% of enterprise sales happen when you’re not in the room
35:13 – How many leads do I really need? A smarter approach to B2B marketing
38:11 – Wrap: What Work-Bench looks for in founders
41:05 – Why unique perspectives and contrarian views stand out
43:03 – Final advice: Find the fun, it’s a long journey
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