Dec 7, 2023 · 20m · top-founders
How I raised a $15m Series B in a downturn
0:00 / 0:00
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
CyberSmart CEO Jamie Akhtar details how his company successfully navigated macroeconomic headwinds to secure a $15 million Series B round through partner-led growth, non-dilutive bridge financing, and disciplined capital allocation.
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 2.5% of the talking time here. How this is scored →
Nathan as informed peer 0.0 Guest teaching 0.0 Guest disagreement 0.4 Nathan pushing back 0.0
speaking balance: gold is Nathan, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 5:20 Dismissing VC expectations of 4x growth
Jamie openly scoffs at venture capitalists who refused to look at companies not growing 3x or 4x yearly during a severe downturn.
Hardest push from Nathan ▶ 0:04 Host pre-roll database promotionBecause the entire core episode is a solo conference presentation without an active host dialogue, the only host audio is Latka's introductory pitch.
Biggest teaching moment ▶ 11:55 Educating audience on predatory term sheet clausesJamie explains why founders must reject 2x liquidation preferences and unfavorable downside protection mechanics inserted by venture funds.
Nathan holds their own ▶ 0:04 Host intro showcasing SaaS metric expertiseLatka presents his SaaS database tracking valuation, CAC, churn, and ARR metrics across thousands of founder interviews.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Nathan as informed peer | Guest teaching | Guest disagreement | Nathan pushing back | Why |
|---|---|---|---|---|---|---|
| Macroeconomic Headwinds and Pivoting to Partner-Led Growth | 0 | 0 | 1 | 0 | This segment is part of an uninterrupted stage presentation by Jamie Akhtar. The host is not present on stage, so host scores are zero. Jamie discusses macroeconomic shifts and pushing back against VCs expecting 3x to 4x growth in a downturn. | |
| Navigating 100+ Rejections and Maintaining Company Morale | 0 | 0 | 0 | 0 | Jamie continues his solo keynote, detailing the emotional and operational toll of enduring hundreds of VC pitch rejections while keeping the team transparently motivated with under three months of runway. | |
| Securing Term Sheets, Valuations, and Negotiating Control | 0 | 0 | 1 | 0 | In this solo presentation segment, Jamie advises founders against predatory term sheet conditions such as 2x liquidation preferences and excessive board seat dilution. | |
| Capital Allocation, Prudent Hiring, and Tech Acquisition | 0 | 0 | 0 | 0 | Jamie breaks down CyberSmart's capital efficiency strategy, emphasizing upskilling existing engineers and making sub-$100k micro-acquisitions over expensive internal tech builds. | |
| People and Finance Leadership and Founderpath Financing | 0 | 0 | 0 | 0 | Jamie closes his presentation by outlining why non-dilutive financing from Founderpath beat restrictive venture debt proposals from SVB, finishing with practical founder takeaways. |
Statements from this episode (11)
Akhtar: Startup funding market will not improve for 12 to 18 months
“So when I set the scene, the last year has been really rough, and as most of you know, it's not going to get any better for the next 1218 months when it comes to the funding market as well.”
Akhtar: CyberSmart burned hundreds of thousands monthly for average revenue growth
“We had a lot of cash, and we were burning a lot of cash, like hundreds of thousands of dollars per month to achieve this kind of revenue growth.”
Akhtar: CyberSmart partner channel achieved 15:1 LTV:CAC and 160% annual NRR
“So our unit economics, our customer acquisition cost lifetime value was one to 15. Our net revenue retention was about 160% a year for partners. And our gross retention was about 99% a month or about 86% a year.”
Akhtar: CyberSmart never had over three months of runway in 2022
“And last year, I don't think there's a single point in the entire year where we had more than three months runway.”
Akhtar: CyberSmart secured four term sheets after repeatedly pitching a rejecting investor
“So we end up with four term sheets in the end and it was really the last one which took a lot of work. I mean, they said no two times, and I kept going back to them every couple months”
Akhtar: VC term sheets increasingly include anti-dilution and coupon downside protections
“Term sheets are much less favorable now, so expect a lot of things in there. If you see anti-dilution, for example, things like coupons as well, it's basically investors just trying to protect from that downside risk but one of the ones we still clear from is …”
Akhtar: Mid-to-late stage UK startups faced 6x to 7x ARR valuation ceilings
“Mid, late stage companies, it definitely looks like there's some kind of ceilings there. We heard from a lot of people, like the six to seven range was pretty standard.”
Akhtar: CyberSmart replaced 18-month cash burn hiring plan with step-and-see model
“We planned to hire, like, 20 to 40 new people in the next 12 months. When we set out, we had our full financial model. We'd have burned through all our cash in about 18 months or so. Since then, we've basically reverted to, like, a more step and see model.”
Akhtar: Founders should buy sub-$100k microacquisitions instead of building features
“The other thing we started looking at, and it's definitely something I encourage all the founders to do, look at microacquisitions. So we used to do a platform called acquire.com, used to go microacquire.com. There's a bunch of platforms like this out there. T…”
Akhtar: SVB offered CyberSmart £3M–£5M debt contingent on closing a round
“This is actually our proposal from SVB.
that we got last year, I think it was about March.
but the strings attached here is like, here, we're going to give you like three to five million pounds, pretty decent interest rate, six and a half to eight percent, b…”