VC Ultimatums, Insider Tracking, and the Reality of Raising Funds | Polysights
In this session, Catherine sits down with Tre Upshaw (Founder/CEO) and Justin Lin (Head of Growth) from Polysights. They pull back the curtain on the psychological warfare of startup fundraising, the transition from Intern to Head of Growth, and why they’re building an intelligence layer to track "insiders" on-chain.
If you’re a builder navigating a term sheet or a user trying to find the signal in prediction market noise, this is for you.
Timestamps:
00:00 Intro
02:41 Finding Polymarket insiders
05:20 The "Day Off" dilemma
06:44 The path from Intern to Head of Growth
09:54 Hiring for startups: What actually matters
13:08 Why build in crypto?
16:30 A newcomer’s POV on the space
18:31 How Army discipline scales a founder
23:10 The brutal reality of raising funds
28:46 Lessons for the next generation of builders
33:48 AI agents and the "average" user
37:51 Growth tactics: How to attract users in 2026
42:44 Can we actually prevent insider trading?
47:50 Radical transparency: Sharing every bet
___________
Follow The Buildooor:
→ Twitter (X): https://x.com/The_Buildooor
→ LinkedIn: / the-buildooor
→ Instagram: / the_buildooor
→ TikTok: www.tiktok.com/@the_buildooor
Also on:
→ Spotify: https://open.spotify.com/show/2NDQCochFaLHJEQ2K9YLAb
5 Mar 2026
Living in one house with your team: crypto co-founder explains why it’s the only way to succeed
“Bitcoiners don’t leave Bitcoin” says OP_NET co-founder Chad Master to chief buildooor Catherine Ross and Chainstory co-founder Tal Shmuel Harel.Watch the latest episode to find out:- why building on Bitcoin could be ‘lonely’, but still crucial- how to maximize your crypto conference hustle- and why you should hire the “Taylor Swifts” of crypto developers for your startup___________Timestamps:0:00 Intro04:03 Chad and OP Net 09:46 Tal’s sad eyes 10:24 Is DeFi on BTC even possible?13:33 Original use case of BTC17:49 BTC as a story of value narrative21:22 Are people still building on BTC?23:12 Challenges of building on BTC 28:50 Being a founder in the Bitcoin space33:30 Why sticking to one narrative is essential to success35:22 Living and building in a hacker’s house41:20 Is it worth going to conferences these days? And how to make the most of it if you do go52:20 Anonymity in crypto: trend or necessity54:40 How to hire efficiently for your team___________Follow The Buildooor:→ Twitter (X): https://x.com/The_Buildooor→ LinkedIn: / the-buildooor → Instagram: / the_buildooor → TikTok: www.tiktok.com/@the_buildooor Also on: → Spotify: https://open.spotify.com/show/2NDQCochFaLHJEQ2K9YLAb
9 Feb 2026
I Raised My Seed Round During the FTX Collapse: Hard Truths with Aya Kantorovich
"I read the news and just slid onto the floor under my desk."
What happens when you’re closing your first funding round the exact week the industry’s biggest exchange implodes? Aya Kantorovich (Co-Founder & Co-CEO of August Digital and UpShift) joins Catherine Ross-Mychka to share the "unfiltered" reality of building in the trenches.
From surviving the FTX contagion to managing two companies simultaneously with a 9-month-old, Aya breaks down the "vaultification" of crypto, why she admits to being a micromanager, and how she uses AI to remove human bias from her management stack.
In this episode, we discuss:
The "Trench" Reality: Surviving the week term sheets were pulled.
Operational Excellence: Why 9-to-5s are dying and how to set real SLAs.
The AI Manager: Using Claude to reclaim 30% of your efficiency.
Founder Balance: Managing two startups and motherhood through "pockets of focus."
Vaultification: Why the future of on-chain asset management is in vaults.
Aya is a relentless buildooor who proves that stress is a privilege - as long as you aren’t bored.
Timestamps:
1:54 VC Perspective vs. Founder Reality
4:33 Why 9-to-5s are dying in crypto
9:10 Running two companies at once
11:50 Making the wrong priority decisions
12:55 The "Micromanager" Hard Truth
17:04 Using AI to remove management bias
20:20 How we use Claude in our startups
22:30 Founder's daily schedule
25:40 Is "Stress" a privilege?
29:39 How a baby made me more efficient
32:20 Raising a Seed round during FTX week
36:15 Hard Truth: It won't get easier
43:30 The "unwind" ritual
48:33 A book every founder should read
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