Skip to main content

How to Properly Evaluate a Startup

Colin B.
By Colin B.Product Lead at Poolside | Scale Your Startup Career Strategically

This 60-minute coaching session gives you a practical framework for evaluating whether a startup is actually a strong career opportunity — beyond the pitch, brand name, or headline valuation. We’ll walk through the key areas you should investigate before accepting an offer, including: - **Business health:** Revenue, ARR growth, burn rate, runway, fundraising history, valuation, customer concentration, margins, and other metrics worth asking the recruiter or hiring manager about. - **Funding and equity:** How to evaluate the company’s funding history, investors, current stage, valuation, and what those factors may mean for your equity. - **Founders and leadership:** How to research the founders, executives, board, previous companies, track record, and leadership reputation. - **Team quality and employee signals:** How to use LinkedIn to understand employee tenure, hiring velocity, leadership turnover, layoffs, and where people go after leaving. - **External research:** How to intelligently use sources like Glassdoor, Blind, Reddit, LinkedIn, Crunchbase, press coverage, and customer feedback without taking any one source at face value. - **Product and market:** How to assess product differentiation, competitive positioning, customer demand, market size, and whether the company has real momentum or mostly hype. - **Startup red flags:** Common warning signs around culture, finances, leadership, hiring, product-market fit, compensation, and unrealistic growth narratives. - **Your specific opportunity:** We can apply the framework directly to a startup or offer you are currently considering and identify the most important questions to ask before making a decision. The goal is to help you perform the kind of diligence on a startup that an investor might — while also evaluating whether it is the right career bet for you.

What's included

1h 30m of coaching$79/hr · Live Sessions$118.50
Total$118.50
  • Which company metrics matter most and how to ask for them.
  • How to distinguish a genuinely strong startup from one that simply interviews or markets itself well.
  • How to assess financial stability, growth, product-market fit, leadership quality, and company trajectory.
  • How to research founders, executives, employees, investors, competitors, and former employees.
  • Which red flags deserve serious concern versus which are normal for an early-stage company.
  • How to think about the risk/reward of joining a startup compared with a larger, more established company.
  • What follow-up questions you should ask the recruiter, hiring manager, or founders before accepting an offer.

Meet your expert

Colin B.

Colin B.

Product Lead at Poolside | Scale Your Startup Career Strategically

1Followers

I've spent my career at the intersection of technology, customers, and product, from small IT consulting firms to MongoDB, AWS, and most recently Poolside, where I joined as the company's first Solutions Architect and later moved into Product leadership. At Poolside, I helped build the global Solutions Architecture organization from 0 to 7 before identifying an opportunity around sovereign AI, building the first prototype myself, and ultimately leading the resulting product line. Over roughly 14 months, we grew it to ~$3M ARR and 40+ deployments across enterprise, government, and highly regulated environments. I've made several career transitions myself, from IT consulting → Sales Engineering → Solutions Architecture → Product, and I've interviewed extensively across startups and large technology companies. I have an MBA from Boston University and particularly enjoy helping people think through career positioning, technical interviews, compensation, startup opportunities, and how to move between technical, product, and customer-facing roles. I'm also an active builder. Outside of work I've launched my own AI-powered market analytics SaaS and built an open-source agent harness. For anyone looking to understand or build with AI, I'm happy to work hands-on across LLMs, agents, cloud architecture, product strategy, and turning an idea into something real.

More offerings from Colin