Money, Power and the Lies You've Been Told About Success

In Episode 3 of the podcast, I sit down with startup founder Ash Hynie to talk about money shame, raising a friends and family round, and what it costs to say no to the wrong check. This post pulls the strongest threads of that conversation together. Note: this post may have affiliate links and we donate 100% of those funds to non-profits and a children's group home🫶🏾

Most of us formed our relationship with money years before we earned any of it. We absorbed it at kitchen tables, in the silence around bills, in the unspoken rule that you never ask anyone for anything. Then some of us started businesses and discovered that the relationship came with us. It shows up in how we price our work, how long we wait to make the ask, how we react when someone goes quiet on us, and whose money we're willing to take. None of that is a personal finance problem. It's a business problem, because every one of those moments has revenue attached to it. My guest Ash, a founder in the middle of raising for her startup, spent a full year in therapy working on this before she could run a fundraise without it feeling like begging. That's the honest timescale, and it's worth understanding why.

You Learned How to Relate to Money Before You Ever Earned It

Ash grew up poor. Not tight-budget poor, but lived-in-a-car, borrowed-food-from-neighbors poor. The lesson she carried out of that childhood was that asking for money embarrasses your family, and that lesson sat quietly in her nervous system for decades until she started a company and had to fundraise. When she asked founders in her network how they approached investors, she noticed the people with easy answers had grown up affluent, mostly white and Asian men who framed the ask as an opportunity being offered rather than a favor being requested. She also realized something that stopped her cold: in startup circles, asking someone for advice is the opening move of a fundraise. People had been treating her questions as soft pitches for years, and she'd been sleeping on capital without knowing the conversation had even started.

I had my own version of that awakening. In February 2018, while I was still at Google, Spotify hosted a Black History Month event in New York about building Black wealth, and I sat in a room full of Black professionals talking about investing, real estate, and generational strategy. What struck me wasn't the tactics. It was watching people who related to money as a tool rather than a threat. I grew up in a house where money was tight and asking for it carried shame, so I'd internalized money as something you survive. That room showed me a different posture existed, and that the difference wasn't intelligence or discipline. It was conditioning, and conditioning can be reworked.

Money Shame Shows Up as Silence

When we ran the friends and family round for moonpaws, the thing that caught me off guard wasn't rejection. It was ghosting. People I talked to constantly, people in my DMs every week, people who had literally said "let me know when you're raising," went completely silent the moment I extended a real invitation to invest. Then, a couple of months later, they'd slide back into my messages about other things as if the unanswered ask had never happened. I've made peace with it, and I understand now that their silence was mostly about their own unresolved stuff with money. But I'll be honest about where I've landed: the people who communicated a clear no are people I'll go back to. The people who gave me the silent treatment won't get a second ask. We're still friends.

That door is just closed.

Ash sees the same pattern from the other side of more repetitions. The people who answered her first raise clearly, whether yes or no, overwhelmingly came from families where money got discussed openly. The ghosting came from people who never learned to say the word "no" about money out loud. Her conclusion is one of the most quotable moments of the episode:

"If you can't communicate a simple yes or no about money at this scale, then it's probably not a good idea that we go into business anyway. We're going to have harder conversations in the future." — Ash

That reframe matters for anyone raising from their community. The silence isn't a verdict on your idea. It's a window into someone else's relationship with money, and it's actually useful data about who can sit with you through the harder conversations a real business will eventually require.

What Money Trauma Does When the Runway Shrinks

Money trauma stays manageable right up until the business gets scary. Winter 2023 was that season for me. The tech industry was shedding jobs everywhere, HmntyCntrd's clients were delaying and canceling contracts, and I watched our reserves drain month after month. I knew in my gut we needed to make cuts early, and shame kept me from acting until the last minute. My business partner and I stopped paying ourselves to keep paying the team. February of that year was the lowest point of my life, and when my business partner finally asked me what I was actually afraid of, the answer that came out surprised me. I said, "I don't want to be like my parents." All of it, the frozen decision-making, the panic, the shame spiral, traced straight back to watching my family struggle with money when I was a kid.

Two people pulled me through that season by reminding me of what was true. My business partner pointed out that the entire body of evidence of my life showed I wasn't headed where my fear said I was headed. And a good friend asked me whether I still believed in what HmntyCntrd was building. When I said yes, he told me, "Then you'll find a way."

And we did.

We got creative with revenue streams in ways comfort never would have forced, and we rebuilt to the point where we took four months off last year and now hold enough in reserve that we could stop working for a year if we chose to. I want to be careful with that arc, though. The scrappiness was real, and I never want my nervous system in that place again. Fear can spark creativity in a crisis. It can't be the operating system.

Not All Money Deserves a Yes

This is the part of the conversation I most want people to sit with. Ash, a Black woman founder in a funding landscape that gives founders like her a sliver of venture capital, keeps a spreadsheet of over 200 potential investors that she is running due diligence on. Read that again. She's vetting them. She knows it looks backwards for someone in her position to be selective, and she does it anyway, because money that doesn't understand the mission will eventually work against it.

"Saying no to money, as hard as it can be sometimes, is necessary. The business grows because there's a need for your solution, and sometimes that takes time. Not all money affords you that time or space." — Ash

I've lived a smaller version of the same principle. A company once wanted to fly us out for live moonpaws events, and during planning they demanded a stack of signed deliverables by the next morning. I could have wrecked my sleep to perform urgency for them. Instead I talked to my partners, named the risk out loud, and we agreed we'd rather lose the contract than train a client to snap their fingers at us.

I told them they'd have everything Monday end of day, since none of this was life or death. They said fine. Of course they did. And if they hadn't, the loss would have been a blessing wearing a costume, because a client who won't honor your humanity in week one will not improve by week twenty. Ash added the caveat that makes this real rather than precious: honoring your values only works if you've actually defined them. Sometimes her values mean running the extra mile. Sometimes they mean rest. Knowing which is which is the maturity the work requires.

How to Heal Your Relationship With Money

Ash's answer to my closing question was blunt: learn more about money. The more you understand how the world moves when money is involved, the less charged the conversations become. Here's where we'd both point you to start.

1. Read The Psychology of Money by Morgan Housel. It opened the floodgates for me, less about tactics and more about the mental shortcuts that quietly sabotage how we hold money.

2. Eavesdrop on other industries. I went through a long stretch of listening to the BiggerPockets podcast. I don't own a real estate portfolio, and it didn't matter. Hearing how investors think about growth and generational wealth rewired my sense of what's normal to talk about.

3. Do the deeper work. The Trauma of Money helped me start untangling the upbringing-level stuff, the shame and the survival patterns that no budgeting app touches. Ash went on a similar journey of this in therapy, and it took her about a year. While it takes time, there’s no better time to start this journey than now.

4. Practice saying the quiet part. Talk about money plainly with people you trust. Ash lends money only in amounts she can afford to lose, tells people so directly, and wants her family comfortable enough to ask her how an investment works. That's what a healthy relationship with money sounds like in a family. It's built one plain-spoken conversation at a time.

Ash and I ended the episode with a bookmark: how you measure your own value when money becomes the yardstick. That's a whole second conversation, and we're going to have it. For now, it's enough to notice whose voice is in your head the next time you name a price, and to ask whether that voice ever built anything.

If money and success are things you're rethinking this season, the newsletter is where I write about it between episodes. Choose courage over comfort with us here.

Originally aired as Episode 3 on the Choose Courage Inc. podcast.