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Mentorship

Mentors Over Mistakes: How to Shortcut Your Startup Struggles

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Ever wonder how some entrepreneurs seem to leap hurdles while others trip over the first? It’s rarely just luck. More often than not, it’s a secret weapon: a mentor. Not a guru on Instagram, but a real person who’s been where you’re heading—and is willing to walk part of that road with you.

From Nairobi to New York, from street food stalls to SaaS startups, mentorship has quietly powered some of the world’s most iconic businesses. Ready to find your own? Let’s dig into why it matters, how to find the right one, and what successful founders have done with this unfair advantage.

Why Mentorship Matters

Starting a business can feel like learning to fly while building the plane. A mentor gives you something more valuable than money: perspective. They’ve seen the road ahead. They know the detours, the shortcuts, and the cliffs you don’t see coming.

Tabitha Karanja, founder of Keroche Breweries in Kenya, often credits the support and informal mentorship of her late husband Joseph Karanja—who had decades of business experience—as pivotal in navigating a male-dominated industry. Starting as a small fortified wine producer, Keroche grew into Kenya’s second-largest brewery, challenging East African Breweries’ dominance. Her mentor didn’t just believe in her—he built with her.

Howard Schultz, former CEO of Starbucks, often mentions Bill Gates Sr., the father of Microsoft co-founder Bill Gates, as a crucial mentor. Gates Sr. helped him navigate the legal and financial complexities of buying Starbucks in its early years. Without that guidance, Schultz admits, he might have lost control of the company.

Lesson? The right mentor doesn’t just advise you—they unlock opportunities, offer protection, and sometimes change your destiny.

What Exactly Does a Mentor Do?

Mentorship isn’t about someone giving you a cheat sheet. It’s about having a sounding board, a mirror, and occasionally, a safety net. A mentor can help you:

  • Avoid expensive mistakes.
  • Refine your pitch and strategy.
  • Build a powerful network.
  • Develop leadership skills.
  • Handle stress, self-doubt, and burnout.

They offer not just knowledge—but wisdom, often hard-won through failure.

Types of Mentors You Might Need

Mentors come in many forms, and most successful entrepreneurs have more than one.

The Industry Insider

They’ve been in your field for years. They know the players, the traps, and the trends.

Anastasia Soare, founder of Anastasia Beverly Hills, got guidance from industry veterans in the fashion and beauty world. These mentors helped her navigate product development and branding in the highly competitive U.S. cosmetics market.

The Technical Expert

They understand the mechanics—finance, tech, legal, operations.

Tunde Kehinde, co-founder of Nigeria’s logistics giant ACE, worked with experienced logistics and supply chain experts across Africa who mentored him on building scalable infrastructure. That guidance helped ACE expand across West Africa.

The Empathetic Listener

They might not have your answers, but they’ll help you find your own. Perfect for handling burnout, imposter syndrome, or team issues.

Where to Find a Great Mentor

Finding a mentor isn’t like shopping for socks. It’s a relationship—not a transaction.

Incubators and Accelerators

Programs like Y Combinator (US), Nailab (Kenya), or Startupbootcamp (Europe) offer structured mentorship. These programs pair startups with seasoned entrepreneurs.

Paystack, the Nigerian fintech company acquired by Stripe for $200 million, benefited from mentorship through Y Combinator. The advice from global fintech veterans helped them sharpen their product and go to market faster.

Industry Events and Networks

Conferences, seminars, and trade shows are great places to meet mentors in your field.

Melanie Perkins, co-founder of Canva, found many of her early mentors through startup events and pitching competitions in Australia. One mentor eventually introduced her to Silicon Valley investors.

Social Media and Professional Platforms

LinkedIn isn’t just for job seekers. Reach out with a thoughtful message—not a generic “Can you mentor me?” but a short, clear ask.

Tip: Say: “I admire your journey building X. I’m currently facing Y in my startup. Would you be open to a 20-minute call so I can learn from your experience?”

University Programs or Alumni Networks

Business schools and universities often offer mentorship programs or connections to successful alumni willing to give back.

How to Build a Relationship That Lasts

Mentorship isn’t just about finding the right person. It’s about being the right mentee.

  • Be Prepared: Respect their time. Come with specific questions or problems.
  • Be Consistent: Follow up, provide updates, and show that you’re acting on their advice.
  • Give Back: Mentors love to see growth. Share your wins, and offer your help where you can—maybe it’s research, connections, or a thank-you shoutout.

Pro Tip: Mentorship is a two-way street. Even experienced mentors learn by teaching.

When Mentorship Goes Wrong (and How to Fix It)

Not every mentorship works out. Some red flags:

  • They dominate the relationship but don’t listen.
  • They push you toward their goals, not yours.
  • They demand equity or money too early.

If it feels off, trust your gut. Be respectful, but don’t be afraid to step away.

A startup founder in India once revealed during a TiE (The Indus Entrepreneurs) panel that a mentor-turned-investor tried to steer the company in a completely different direction to suit his own portfolio. The founder had to sever the relationship and lost time—but ultimately saved the company.

How Mentorship Shaped Iconic Businesses

Here are a few examples of how mentorship propelled businesses around the world:

Alibaba (China)

Jack Ma, founder of Alibaba, credits early mentorship from foreign businesspeople and English teachers, especially those he met while giving tours in Hangzhou, with shaping his international business mindset. Later, investors like Masayoshi Son of SoftBank played mentorship-like roles during Alibaba’s rapid scaling.

Airbnb (USA)

Airbnb founders Brian Chesky and Joe Gebbia were mentored by Paul Graham of Y Combinator. Graham didn’t just invest—he pushed them to “do things that don’t scale,” like personally photographing hosts’ homes to create trust on the platform. That mindset became a cornerstone of Airbnb’s growth.

Jumia (Nigeria)

As one of Africa’s leading e-commerce platforms, Jumia’s founders relied heavily on mentorship and guidance from Rocket Internet’s leadership, whose experience in global logistics, hiring, and operations helped Jumia scale across the continent.

The ROI of a Mentor: Priceless

Having a mentor isn’t about shortcuts. It’s about sharpening your instincts, expanding your worldview, and making fewer costly mistakes. Most entrepreneurs will face cash crunches, bad hires, and failed launches. A mentor helps you survive—and thrive—through them.

Even top-tier investors look for founders who listen—and having a mentor signals humility and coachability.

What If You Can’t Find One Right Away?

Not everyone finds a perfect mentor early on. In the meantime:

  • Read biographies and listen to founder podcasts.
  • Join peer-mentoring groups (like Founders Network or local chambers).
  • Watch TED talks and interviews with successful entrepreneurs.
  • Write down your biggest challenges and how others might approach them.

Sometimes the first mentor is a virtual one.

Don’t Go It Alone

Entrepreneurship can be exhilarating—but it’s also lonely, confusing, and filled with decisions that feel like life-or-death. A mentor doesn’t eliminate the hard parts—but they make them easier to navigate.

Find someone who believes in your vision, challenges your assumptions, and walks beside you—not ahead of you.

Because the truth is this: Every self-made entrepreneur had help.

Now it’s your turn.

Justin Kasia

Social impact. Supporting startups.