IJLMI: Into Impact with Ashley Kirkwood
In this episode of I’ll Just Let Myself In, host Lish Speaks sits down with powerhouse attorney, entrepreneur, and speaker Ashley Kirkwood to talk about impact, resilience, and building systems that truly change lives. Ashley, founder of Speak Your Way to Cash, shares her journey from aspiring talk show host to corporate lawyer, to finally carving her own lane as a sought-after speaker and coach who equips others to monetize their voice.
From Law to Legacy
Ashley’s story begins with a childhood dream to follow in the footsteps of Oprah. Though she felt called to speak and encourage others, her parents encouraged her to pursue law school first. Determined not to abandon her gifts, she juggled her legal ambitions with a passion for communication. That persistence paid off—despite a rocky academic start, she went on to graduate cum laude from Northwestern University School of Law and work at one of the largest firms in the world.
But the high-paying job came at a cost. When she switched firms for an even bigger salary, Ashley immediately felt out of place. The toxic environment pushed her to reassess her path, and that leap of faith birthed Speak Your Way to Cash. What started with bulk book sales and small speaking engagements blossomed into a multi-million-dollar business helping entrepreneurs, especially Black women, transform their stories into income.
Building Skills, Not Just Dreams
One of Ashley’s most powerful lessons is the distinction between gifts and skills. Many entrepreneurs, she explained, rely on raw talent or spiritual gifts without taking the time to sharpen them into tangible, marketable offers. “Even Jesus perfected a skill,” Ashley noted, reminding listeners that preparation is essential for sustainability.
Her advice is clear: don’t just dream big—do the work. Whether it’s creating systems, packaging an offer, or learning how to pitch effectively, Ashley emphasizes that long-term success comes from intentional skill-building. She encourages believers in particular to avoid the trap of selling their gifts instead of creating real, valuable offers.
Overcoming Setbacks and Raising Standards
Ashley’s rise wasn’t without obstacles. She shared candidly about being arrested in college, nearly failing out of undergrad, and facing rejection from law schools. Yet each setback became a stepping stone. “If you don’t get in the first time—apply again,” she said. Her persistence not only got her admitted into Northwestern but also set the tone for how she approaches every challenge.
Another standout moment was her recent sold-out event in London. With her husband and videographer unable to make the trip, Ashley had to navigate the entire event alone. From hiring a replacement team on the fly to even firing someone on site, she learned the importance of maintaining her standards no matter the circumstances. That unwavering commitment inspired attendees who witnessed her lead with both authority and grace.
Faith, Family, and the Bigger Picture
While Ashley is relentless in business, she’s equally intentional about her family. She and her husband, partners in life and work, have built their business while raising their daughter, ensuring she sees entrepreneurship modeled firsthand. Ashley stressed the importance of family planning, delegating responsibilities, and creating systems at home just as in business. Her daughter has already traveled the world, joined in speaking events, and learned by example what it means to carry high standards.
At the core of Ashley’s message is the belief that impact is holistic. It’s not just about financial wins, but about faith, family, fitness, and legacy. She openly admits to balancing pressures like payroll, client expectations, and the demands of motherhood, but insists that God’s strength equips her to do what she could never accomplish alone.
Deciding to Invest in Yourself
Toward the end of the conversation, Ashley challenged listeners to consider where they stand: doubters, dabblers, or the decided. Those who truly commit, she says, are the ones who invest in themselves, join masterminds, and put money behind their dreams. Speak Your Way to Cash has grown because she not only practices what she preaches but also equips others with proven systems to create sustainable impact.
For anyone wrestling with doubt or waiting for the “perfect moment,” Ashley’s story is a reminder: the time is now. Don’t wait for permission. Don’t settle for mediocrity. Do the work, build the skill, and step boldly into the impact you were created to make.
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TIMESTAMPS
0:00 – Introduction: Lish Speaks on letting yourself in
1:25 – Meet Ashley Kirkwood: Attorney, entrepreneur, speaker
3:00 – Childhood dreams, Oprah inspiration, and the road to law school
7:00 – Overcoming rejection and setbacks on the path to Northwestern
10:00 – Lessons from law school and corporate law career
15:30 – Leaving a toxic firm and birthing Speak Your Way to Cash
18:00 – First speaking engagements and building a business from scratch
19:30 – International events in Ghana and London
22:00 – Learning resilience: managing pressure and standing on standards
25:00 – Releasing the need to be liked and holding firm boundaries
28:00 – The importance of rest, productivity, and protecting your peace
30:00 – Faith, family, and balancing multiple roles as wife, mom, and CEO
34:30 – Evolving into the next version of yourself
37:00 – Marriage, family planning, and building with a supportive partner
41:30 – Modeling success and standards for her daughter
46:00 – Speak Your Way to Cash framework: turning gifts into skills
50:00 – Avoiding emotionalism: building systems that sustain
56:00 – Why investing in yourself matters: doubters, dabblers, and the decided
1:01:00 – Saving the life you’re meant to live by betting on yourself
1:05:00 – Closing reflections: stepping boldly into impact
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