Meet Annemarie Penny | Founder & CEO, Dreamore – Recruiting & Advisory for Startups

We had the good fortune of connecting with Annemarie Penny and we’ve shared our conversation below.

Hi Annemarie, what is the most important factor behind your success?
Authenticity. In my early career, I had a “business persona” that wasn’t nearly as fun as my “weekend persona”. I did a good job, but I was only an average employee. When I launched my first recruiting business, I didn’t want that feeling of separation anymore. I wanted to fully BE MYSELF. I picked an industry I was genuinely excited about (tech startups) so the conversations felt natural. Many of my clients became friends. I built up a reputation for sharing joy and not simply being another high volume, transactional firm. I’ve entertained in my home for decades now, bringing together “commerce, community, and creativity”. Authenticity feels even more crucial now that the business world is on social media, working remotely, and using AI. You don’t have to go as far as I have, making friends of your clients and opening up your home like I’ve done. Authenticity still needs boundaries 🙂 No matter how you express yourself truthfully, I can assure you it will be noticed, and it will resonate deeply with the trustworthy people (and clients) that you need in your life.

Alright, so let’s move onto what keeps you busy professionally?
I came to California as a teenager with $200, a car, and a place to sleep for a few weeks. From that modest beginning, I built up a recruiting & advisory business for startups that landed our little firm on the Forbes list, surrounded by some of the biggest names in the industry. I was mentored excellently in the early days. I have always passed along the gift of mentorship back to people I’ve hired in my company and to various clients/younger people.

Recruiting can be a very transactional business. I never did it that way. It’s all about authentic relationships. Towards that goal, I have also been a community leader, hosting numerous events in my home and bringing people together for fun, bonding, and business. I was a very shy and serious child, so I think I am making up for lost time! and the positive impact you can make for others, more than offsets the fear that you will do something wrong.

I look for silver linings even when times feel dark. That was particularly tested in 2018. The year began with me sitting with a young friend in ICU with a rare cancer. She passed soon thereafter. The year ended with the Woolsey fire taking our beloved “Malibu Dream House” and with it- my sense of identity, and a great loss for all the friends and clients who’d enjoyed it over the years. I took the following year to rest and heal. I’d always had a sense of scarcity. Even when I had worked hard and gained so much. Losing “everything” helped me remember what I still had – relationships – and what actually matters – not all this “stuff”.

I relaunched my company after all of that, with a new name Dreamore, to reflect my restored sense of purpose and also to better describe our goals in supporting startups that are doing something good for the world and their people, particularly uplifting women & underserved groups.

The last few years have seen numerous challenges in hiring and the economy. Not everyone has suffered, but many have. Remote work, AI, and other dynamics have created some isolation or loss of identity. So I am here (along with my team) to “put the humanity back into hiring” – continuing to put positive energy into my sector, bring people together in community, and build companies with people in ways that will elevate business and encourage sustainable growth into this next cycle.

Dreamore is also the name of 10 acres of land I’m developing – not the same place that burned, but definitely phoenix-from-ashes energy. Ultimately I will live there, share the space with others, and nurture gardens for healing (people AND planet)

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
I would take a road trip up the coast – first stop in Manhattan Beach where I used to live, perhaps a walk or rollerblade on the Strand and watch some volleyball. Pancho’s for margaritas! Second stop in Santa Monica, stroll the pier even if it’s a bit crowded and touristy, and hopefully see some slackliners or aerialists on the beach. Either Blue Plate Oysterette or Casa del Mar for appetizers or a full meal. Keep heading north – Dreamore is my land at the top of Topanga, surrounded by the conservancy and the ocean, and I’d show them my private hiking trails down into Tuna Canyon, plus a sunset glass of wine sounds just fine. If we have the entire weekend for a fuller California coastal experience, then we’d HAVE to head up to Santa Barbara, Paso Robles wine country, and then over to Hearst Castle and Big Sur. There’s no better fine dining experience that the restaurant at Post Ranch Inn, right on the cliffs so hopefully you’re not afraid of heights! If we can’t get that far north….or budgets are tight… well at least Schooners in Cayucos will give a nice view and delicious food/drinks, without fail.

Who else deserves some credit and recognition?
Kyle Hollingsworth, host of CourageousAF podcast, a talented creative director and fine artist, a resilient and inspiring human being who always Keeps It Real

Website: https://dreamore.io

Instagram: dreamoredreams

Linkedin: https://linkedin.com/in/annemarie

Twitter: dreamoredreams

Facebook: dreamoredreams

Youtube: dreamoredreams

Other: https://dreamore.beehiiv.com

Image Credits
All images taken by me, Lydia Thompson in my company, or the one architectural photo is a rendering from Tim Gorter, architect