10 Red Flags That Signal a Bad Startup Advisor (From Someone Who Learned the Hard Way)
I’ve been on both sides of the table. As a founder, I’ve worked with over 20 startup advisors. As an investor, I’ve advised more than 40 companies. But my most valuable experience? Losing $200,000 to a “startup advisor” who showed every red flag I’m about to share with you.
Through our work at Do Not Work With (DNWW.io), we’ve analyzed thousands of advisor relationships gone wrong. Here are the patterns that emerge consistently.
1. The “Too Good to Be True” Network
What It Looks Like: They claim to be “best friends” with every top VC and founder in Silicon Valley. Their LinkedIn shows advisory roles at multiple unicorns, yet something feels off.
Real Example: Last month on DNWW.io, three founders reported the same advisor who claimed to be “close friends” with a famous VC. When they finally got their intro call, the VC had never heard of them.
2. The Urgency Pusher
What It Looks Like: They pressure you to sign agreements quickly, citing “other opportunities” or “limited availability.” They make you feel like you’ll miss out if you don’t act now.
Warning Sign: Good advisors are busy, yes, but they want you to do proper due diligence. They respect your need to verify their credentials and references.
3. The Vague Value Proposer
What It Looks Like: They speak in broad generalities:
- “I’ll open my network to you”
- “I’ll help with strategy”
- “I’ll accelerate your growth”
What You Want Instead: Specific, actionable commitments with measurable outcomes.
4. The Equity Grabber
What It Looks Like: They ask for significant equity (>1%) upfront, before proving value. They might justify it with their “standard terms” or “what they usually get.”
Data Point: Our analysis at DNWW.io shows that the most successful advisor relationships start with 0.1-0.25% equity, vesting over 2 years with a 6-month cliff.
5. The Reference Dodger
What It Looks Like: When you ask for references, they either:
- Provide only their closest friends
- Claim confidentiality prevents sharing
- Give you one or two superficial contacts
Protection Tip: Always check DNWW.io for independent reviews and experiences from other founders.
6. The Past Glory Dweller
What It Looks Like: They constantly reference achievements from 5+ years ago. They can’t point to recent, relevant successes in your space or stage.
Why It Matters: The startup ecosystem changes rapidly. You need an advisor who understands today’s challenges, not yesterday’s solutions.
7. The “I Know Everything” Expert
What It Looks Like: They claim deep expertise in every area:
- Product development
- Marketing strategy
- Fundraising
- Technical architecture
- International expansion
Reality Check: The best advisors are clear about what they do and don’t know. They’re happy to refer you to others for areas outside their expertise.
8. The Availability Avoider
What It Looks Like: During discussions, they’re extremely responsive. After signing, they’re suddenly “swamped” or “traveling” whenever you need help.
Protection Strategy: Set clear expectations about communication frequency and availability in your advisor agreement.
9. The Information Trader
What It Looks Like: They seem too interested in your internal metrics, team dynamics, or proprietary information. They might advise your competitors or be gathering intelligence for their own ventures.
Real Story: A founder in our DNWW.io community discovered their advisor was sharing confidential growth metrics with competing startups in exchange for equity.
10. The Non-Listener
What It Looks Like: They give the same advice to every company, regardless of context. They talk more than they listen and dismiss your specific challenges.
Warning Sign: If they’re giving you detailed advice before understanding your business, they’re not really advising – they’re selling.
How to Protect Yourself
Before bringing on any advisor:
- Check their background on DNWW.io
- Get references from current (not just past) advisees
- Start with a trial period before granting equity
- Document specific deliverables and expectations
- Trust your instincts if something feels off
The True Cost of a Bad Advisor
It’s not just about the equity you give away. Our data at Do Not Work With shows the average cost of a bad advisor relationship includes:
- 6-8 months of wasted time
- $50,000-200,000 in missed opportunities
- Damaged team morale
- Strained investor relationships
Final Thoughts
The right advisor can transform your startup. The wrong one can set you back years. Before you sign that advisor agreement, check DNWW.io to see if others have had experiences with them – good or bad.
Remember: It’s better to have no advisor than a bad advisor.