Feb 14, 2018 · 19m · top-founders
935 How to Reset After Raising $27m and Hiring Too Fast
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In this episode of The Top Entrepreneurs Podcast, Nathan Latka interviews InsightSquared CEO Fred Shilmover about raising $27 million in venture capital, navigating a difficult headcount reset after rapid expansion, and scaling a specialized sales analytics platform to over 750 mid-market and enterprise clients.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 36.7% of the talking time here. How this is scored →
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Fred explicitly dismisses Nathan's premise comparing InsightSquared to acquired social tools like Wildfire and Buddy Media, asserting those businesses share no interconnect with his sales analytics focus.
Hardest push from Nathan ▶ 4:00 Nathan refuses to accept Fred's pricing deflectionNathan interrupts and repeatedly insists that Fred must provide a pricing floor, asking if it's a dollar, a thousand, or a million to protect prospective buyers from opaque sales tactics.
Biggest teaching moment ▶ 11:18 Fred educates Nathan on sales tech vs. marketing tech categoriesFred explains the nuances between general BI, martech, and sales enablement, illustrating how sales technology is undergoing a major transformation a decade after marketing tech did.
Nathan holds their own ▶ 9:18 Nathan presents counter-thesis on venture funding time bombsNathan counters Fred's positive spin on not raising capital recently by citing the venture model expectation that funded companies should raise every 12 to 18 months toward an IPO or risk struggling.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Introducing Fred Shilmover and InsightSquared | 5 | 2 | 3 | 7 | Nathan relentlessly drills Fred to reveal pricing or average contract value, directly challenging Fred's decision to gate pricing on their website. Fred remains calm and repeatedly deflects without disclosing specific dollar figures. | |
| Founding InsightSquared and the Decision to Raise VC | 6 | 6 | 4 | 5 | Nathan challenges Fred on why he didn't bootstrap like other successful founders (citing Qualtrics). Fred clearly breaks down the trade-offs of heavy upfront R&D engineering investment versus bootstrapping. | |
| Managing Headcount Resets and Pursuing Sustainable Growth | 6 | 3 | 3 | 6 | Nathan pushes Fred on historical layoffs, VC timeline pressure, and timeline to profitability, even challenging Fred's reluctance to discuss the P&L on air. Fred acknowledges past over-hiring while defending their path to sustainable growth. | |
| Specialization in Sales Analytics vs Generic BI | 4 | 7 | 5 | 3 | Nathan asks why InsightSquared didn't exit during the 2012 social media wave, grouping them with Wildfire and Buddy Media. Fred corrects Nathan's categorization by demonstrating that InsightSquared is a sales analytics company rather than social marketing tech. | |
| Modern Sales Tech Stacks and Customer Traction | 6 | 3 | 2 | 4 | Nathan brings up Mattermark and data enrichment tools to test Fred's positioning and presses for ARR milestones. Fred elaborates on how modern sales stacks operate and confirms passing 750 customers while politely declining revenue metrics. | |
| The Famous Five Rapid-Fire Questions | 2 | 1 | 1 | 1 | A collaborative Famous Five rapid-fire segment where Fred shares insights on favorite books, sleep habits, and learning that human decisions are emotional rather than purely rational. |