If you’re afraid to cold-call, don’t start a business

If you’re afraid to cold-call, don’t start a business—connecting with people outside of your network is essential for growth.

I have cold-called alumni as a student fundraiser, prospected into mid-sized companies with a need for cloud storage, emailed entrepreneurs to build relationships as a venture investor, approached industry experts on LinkedIn, and recruited engineers and designers for Salesroom on Instagram and Twitter.

Every job I’ve ever had has required some form of lukewarm outreach at a minimum. Here’s what I’ve learned:

• Make your message personal and specific—you’re far more likely to get a response. Asking for 30 minutes to exchange views on X is more intriguing than a generic message about a coffee chat.

• Acknowledge that you’re reaching out cold, but clearly state why you think there’s a compelling reason to connect. Transparency and clarity build trust.

• Do your research to catch people where they are most open to having a conversation. Different people have different ways they prefer to be contacted—Twitter, LinkedIn, conventional email (but few people respond well to a cold phone call without any written intro).

• Channel authenticity. Infuse your individuality into your outreach so you don’t come across as just another sales call to filter out. Speaking of filtering, I begin all my cold emails asking not to be marked as spam because it will damage our domain reputation :) This simple and earnest request helps manage risk with cold outreach.

• Be open when other people reach out cold to you. Generosity and paying it forward foster growth for everyone!

• When someone agrees to speak with you, invite them to lunch (when it feels fully safe and comfortable to do so). I have yet to meet someone who turns down a free lunch.

• If someone agrees to speak and then goes radio silent, follow up! People are busy, and you’re not their priority (yet). There’s no shame in a quick message to remind them of your engagement.

• Always follow up with a thank-you note. Genuine appreciation never fails. Match the level of gratitude to the interaction—a friendly email for a brief chat, a handwritten note—or even a gift—for a pivotal milestone.

• Don’t take rejection personally! If someone isn’t getting back to you, they’re most likely busy or not open to new connections—not singularly declining you.

• Don’t psych yourself out. In my experience, it’s exceedingly rare that a cold call will elicit an angry or unpleasant response. In an outlier case, I was once accused of industrial espionage, and my inner James Bond rejoiced!

What are your strategies to connect with people you don’t know? Let me know in the comments!