How to Scale Your Startup to $1 Million: Lessons from an Email Deliverability Expert

Look, I get it. You’re probably rolling your eyes at the mention of a cold email. Trust me, I was skeptical too.

I recently had a chat with Benny Rubin, and it completely changed my perspective. Benny’s the founder of Senders, a company that basically ensures your emails don’t end up in digital purgatory (aka the spam folder).

We dove into the nitty-gritty of how email has evolved since the early days (we’re talking 2007, when dinosaurs roamed the internet). Benny dropped some serious knowledge bombs about why most startups are screwing up their email game, and how you can avoid those pitfalls.

So grab a coffee (or something stronger, I won’t judge), and let’s dive into what I learned from Benny. Trust me, whether you’re a cold email skeptic or a die-hard believer, you’re gonna want to hear this.

The Email Landscape Has Changed Dramatically

If you haven’t done cold email outreach in a while, brace yourself. The game has changed significantly over the past decade:

  1. Legal gray areas remain, but sender tolerance is lower
  2. Google and Microsoft are far less tolerant of high-volume sending
  3. Inboxes are less cluttered with internal communications
  4. More businesses are doing cold email, increasing competition

The upshot? You need to be more strategic and thoughtful in your approach.

Differentiation is More Critical Than Ever

With the proliferation of SaaS products, it’s harder to stand out. As Benny notes:

“The chances that your product or service is actually unique to the person that you’re emailing is very, very low.”

This means you have to work harder to differentiate yourself, both in your product offering and in how you communicate its value.

Focus on Building Genuine Rapport

One of Benny’s key insights is that success in B2B sales comes down to your ability to build rapport. This is especially crucial when dealing with generational differences:

“If they’re very good at building rapport, then age and generation completely dissolves. And if they’re not that great at building rapport, then age differences become exacerbated.”

How do you build rapport via email? By asking thoughtful questions, truly listening to responses, and tailoring your approach accordingly.

The Power of Niche Expertise

When scaling your startup, surround yourself with people who are absolute nerds about their domain. As Benny puts it:

“You want the people that are absolute nerds about things around you. That’s what you want.”

This applies to your team, your service providers, and even the tools you use. Seek out and leverage deep expertise.

Don’t Underestimate the Size of the Market

Many founders give up too quickly on channels like cold email because they think they’ve exhausted their target market. Benny cautions against this mindset:

“The size and scope of the U.S. economy is breathtaking in its enormity. Folks tend to think, well, on Apollo or on whatever, my database, there’s 10,000 people in my target market. That’s my entire target market. We email them all once or twice or three times and then we sort of tried that.”

In reality, there’s likely a much larger addressable market than you realize. Don’t give up too quickly.

Tailor Your Messaging to Millennials

As Benny points out, millennials now control many of the budgets in B2B sales. Yet much of the messaging out there doesn’t resonate with this demographic:

“More and more and more, I’m realizing how many marketing and sales messaging decidedly does not resonate with me or the sort of millennials in my space.”

Make sure your cold email copy speaks to the pain points and priorities of millennial decision-makers.

Practical Tips for Cold Email Success

  1. Keep it short and simple. Get to the point quickly.
  2. Make declarative statements. Avoid weasel words.
  3. Be unorthodox. Stand out from the sea of sameness.
  4. Structure your emails clearly. Make them easy to skim.
  5. Show empathy. Center your message on the reader’s problems.

The Importance of Email Deliverability

All the clever copywriting in the world won’t matter if your emails don’t reach the inbox. That’s where deliverability comes in. As you scale your outreach efforts, consider working with experts like Senders who can ensure your messages actually get delivered.

Look Beyond Email

While email remains a powerful channel, don’t put all your eggs in one basket. Benny notes that successful companies often use a mix of:

  • Email outreach
  • Cold calling
  • LinkedIn outreach
  • Conferences
  • Inbound marketing
  • Other forms of outbound marketing

Experiment to find the right mix for your business.

Embrace the Entrepreneurial Journey

Scaling a startup is hard work. It’s easy to get bogged down in the day-to-day minutiae. But as Benny reminds us, it’s important to step back and remember why we do what we do:

“At the end of the day, most people like me are in the business of trying to figure out how to help someone with something that you’re significantly better at than they are.”

Focus on providing genuine value, and the growth will follow.

The Power of Persistence

Building a seven-figure business doesn’t happen overnight. It requires consistent effort over time. As Benny notes:

“You can basically win by working harder, working smarter, being more in touch with people on a genuine human level and squirreling hard to build your business and sort of do an okay job just ignoring almost anything else that’s happening around you.”

Don’t get discouraged if you don’t see immediate results. Keep refining your approach and pushing forward.

Cultivate Empathy and Creativity

To truly connect with prospects and stand out in a crowded market, you need to tap into your empathy and creativity. Benny recommends reading fiction to help with this:

“If you read fiction it improves your empathy, because you’re exposing your brain to different perspectives.”

This improved empathy can translate directly into better leadership and more effective sales and marketing.

Summary

Scaling your startup to $1 million in revenue is a challenging but achievable goal. By leveraging cold email effectively, focusing on building genuine rapport, embracing niche expertise, and persistently refining your approach, you can accelerate your growth.

Remember:

  • The email landscape has changed – adapt your strategy accordingly
  • Differentiation is crucial – stand out from the crowd
  • Build real rapport with prospects
  • Don’t underestimate your market size
  • Tailor your messaging to millennial decision-makers
  • Ensure your emails actually get delivered
  • Look beyond email to a multi-channel approach
  • Stay focused on providing genuine value
  • Cultivate empathy and creativity to connect better

Now get out there and start scaling! And if you need help with email deliverability as you grow, check out Senders.co or connect with Benny Rubin on LinkedIn.

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