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Small Business. Big Ideas.

Main Street

Twenty years ago, Penelope Larry had a dream to open a men’s clothing store. It would be called The Art of Shoes. There’d be pedicures in the back and high-quality, supportive shoes in the front. She thought men needed help taking care of their own feet — “We spend so much time on them,” she says. “The feet carry so much weight, literally and figuratively.”

Penelope’s dream lay dormant as she went on with life, to a happy marriage and family. Then, a few years’ back, one of her husband’s friends told her of a business opportunity in Sacramento’s North Highlands, a men’s clothing store. She had been teaching part-time at Sacramento State. “So I didn’t return for the spring semester and went full-time into my business.”

Penelope’s education came before the rise of social media as a preeminent way to reach customers. When the COVID-19 pandemic shuttered her new endeavor, Distinguished Gentleman, she needed to pivot to online, as quickly as possible. She’s looking for mentorship to help her navigate the business’ many new challenges.

Comprised largely of locally owned companies and solo-entrepreneurs like Penelope Larry, Sacramento’s “Main Street” is a vibrant patchwork of restaurants, retail shops, and service-oriented businesses. While many of these owners of small shops are doing their best to respond to the effects of the pandemic, time constraints and limited access to professional networks and resources can be isolating and stressful. Mentor Sacramento will connect Main Street Entrepreneurs to helping hands who can meet them where they are in their business journey — whether that’s managing cash flow, untangling financial statements, attracting customers, or planning for a pivot to online sales — and on their own schedule.

Join our free community of entrepreneurs and volunteer mentors.

  • 1. Create a Profile on Mentor Sacramento

    A complete profile is the first step to connecting with business mentors. It’s who you are and why you’re here. The quality of your profile makes an important impression on your potential connections.

  • 2. Reach Out to Others and Connect

    Explore members who have the profile you're looking for. Reach out by sending messages to several members. Start a conversation and find the right fit for you.

  • 3. Start Mentoring

    Now that you've found a match, ask questions, share, and listen. Agree on how and when to communicate using email, video chat, or a phone call. Set goals and start solving problems together.


I’m a risk taker, and I also have some experience in the school of hard knocks. I want to learn to market in a way that I can dominate my area.

Penelope Larry, owner, Distinguished Gentleman