Simon Says

Ortavia Simon Founder · Speaker · Simon Says

Simon says don’t you dare quit.

I started with no runway, no network, and no permission — only the refusal to stop. Simon Says is the name I put on everything I build, because saying the thing out loud is the part that finally moves it. This is the honest account of how it went, and the instruction set I’d hand you if you were sitting across the table.
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Ortavia Simon in a charcoal suit against a pale studio backdrop
Simon Says

Simon says — first, the nameTwo words, and a whole way of working.

In the playground version, nothing moves until Simon says so. You wait, you listen, and someone else decides when you get to take a step. Grown up, the game runs backwards: there is no Simon, no whistle, and no one left to give the order. You are the one who has to say it.

So Simon Says became the name on everything — the talks, the mentoring, the businesses, the videos. It is a reminder that a plan is not a plan until it is said out loud to a person who will ask you about it later. Say it, then do it, then say the next one.

It is also literally the family name, which is the part I like most. Every business below carries Simon on the door, and every one of them started as a sentence somebody said out loud before there was any evidence for it.

Simon says — the hard partNobody is coming to hand you the door.

Most advice about building something assumes you already have the things that make building easy. Capital. Contacts. A safety net that catches you the first three times you fall. I didn’t have those, and I stopped waiting for them.

What I learned is that persistence isn’t a personality trait you are born with. It’s a decision you make again on a bad Tuesday, and then again the Tuesday after that. That’s the whole secret. It’s less inspiring than people want it to be, and far more available.

So I don’t teach shortcuts. I teach the part nobody films: what to do on the day it isn’t working, when quitting would be completely reasonable and nobody would blame you for it.

Ortavia Simon seated in a warmly lit sitting room, laughing mid-conversation

Simon says — out loud, in orderSix things I say until they stick.

The short list I repeat in every room, on every call, to every founder in their first two years. Nothing here is theory.

  1. Rule one

    Simon says start before it looks ready.

    Ready is a feeling that arrives after the work, not before it. The first version being embarrassing is the toll, not the verdict.

  2. Rule two

    Simon says say it to a witness.

    A goal kept in your head is a mood. Told to one person who will ask you about it on Friday, it becomes a deadline with a face on it.

  3. Rule three

    Simon says do the boring half first.

    The filing, the follow-ups, the invoice nobody chased. The unglamorous half is where the compounding actually happens.

  4. Rule four

    Simon says count the days, not the wins.

    Wins are lumpy and mostly out of your hands. Days shown up are yours, and they are the only number that predicts the rest.

  5. Rule five

    Simon says quit the plan, not the point.

    Changing how you get there is not failure. Most of what I run today is the third or fourth attempt at the same stubborn idea.

  6. Rule six

    Simon says leave the door open behind you.

    Somebody eventually said something to me that kept the lights on. Part of every week goes back to doing that for someone else.

Simon says — where to find meWhere I show up

Speaking
Keynotes and panels for rooms full of people deciding whether to start. Best suited to audiences who are past motivation and want the mechanics.
Mentorship
Working directly with a small number of founders in their first two years — the stretch where most people quietly stop.
Building
Still running the businesses, still in them daily. Everything I teach is something I am currently doing, not something I did once.

Simon says — the receiptsThree businesses, one name on the door.

One saying, three front doors. Each of these is a working business, not a side project — and each one is where the rules above got tested.

Simon Law Group, P.A. logo

LegalSimon Law Group, P.A.

A Florida law firm handling wrongful death, funeral home and cemetery disputes, and personal injury — serving Orlando, Winter Park, Kissimmee and Sanford.

Stafford & Simon Family Funeral Home, LLC logo

Funeral careStafford & Simon Family Funeral Home

A family-run funeral home serving Orlando and Deland — burial, cremation and memorial services carried out with the plain honesty families deserve on the worst week of their lives.

Simply Simon Properties, LLC logo

Real estateSimply Simon Properties, LLC

The simple approach to real estate investments — renovation loans, tax deed sales, short- and long-term rentals, and fix-and-flip properties, explained before you sign anything.

Simon says — press playThe Simon Says Podcast

A monthly show about business and entrepreneurship, for the builders, the dreamers, and the ones who refuse to quit.

Simon Says Podcast cover art: the wordmark in gold and ivory over a portrait of Ortavia Simon at a microphone

The podcast is the saying with the microphone on. Each episode goes at business growth, failure, risk and setback directly — and at the mindset it takes to keep moving when the thing you tried did not work. It is the same instruction set as the rest of this page, talked through at length instead of listed.

If you have failed while chasing a goal, questioned whether you are on the right path, or felt stuck while knowing you were meant for more, this is aimed at you. Not motivation — mechanics, told by someone still running the businesses. Elevated mindset, relentless pursuit.

  • Entrepreneurship
  • Building a business
  • Success mindset
  • Money management
  • Investing
  • Personal growth
  • Giving back
  • Mistakes, failures & the comeback
  • Turning vision into reality
  • New episodes monthly
  • Hosted by Ortavia D. Simon, Esq.

  1. Episode 1 · 91 min

    Business, exposure, investing and the moments where success feels unclear

    Entrepreneurship comes with risk, growth comes with failure, and success comes from refusing to quit — but social media makes it easy to chase an illusion instead of an impact. On spotting what is actually authentic, and building substance rather than a lifestyle nobody earned.

  2. Episode 2 · 33 min

    The right doors, real vision, navigating capital, and the courage to wait

    What building looks like when capital is not guaranteed and the path is not clear. Walking away from the wrong deals, learning to state your vision plainly enough that people can back it, and understanding that a delay is not always a denial.

  3. Episode 3 · 63 min

    Faith, entrepreneurship, and building purpose-driven businesses

    A conversation with Pastor David Jacques of The Kingdom Church in Orlando, on building a business without trading away your values to do it — and on where faith actually meets decision-making, resilience and legacy.

Simon says — tell it straightThe part that didn’t go smoothly.

Told in order, including the years I’d rather skip.

Year one

The decision nobody applauded

Where it started, what I walked away from to do it, and the first time I said the plan out loud to somebody who could have talked me out of it.

The middle

The stretch with no evidence

The long run of work that produced nothing visible — and the reason I kept going anyway, which was mostly that I had already told people I would.

The turn

The first thing that worked

What finally moved, why it wasn’t the thing I expected, and how the same saying ended up on the second door and then the third.

Now

Handing it forward

What I am building today, and why I spend part of every week on other people’s beginnings instead of my own numbers.

Ortavia Simon seated in a black suit against a dark studio backdrop, hands clasped, looking straight at the camera

Simon says — word for wordFour lines I keep coming back to.

“Nothing amazing happens on the shore; it all happens in the deep end.”

“Success isn’t about what is in your bank account; it’s about what’s on your balance sheet.”

“To never quit chasing your goals, you have to want success more than you want breath.”

“Success requires you to have a will not to quit.”

Simon says — your turnStart where you actually are.

Not where you’d like to be, and not once you feel ready. Leave your email and I’ll send you the practical version — how people without a head start actually get a business off the ground.

Ortavia Simon standing in a black suit and tie against a dark studio backdrop, hands in pockets

Or come watch instead

New videos on what’s actually working in business right now — the tactics, the numbers, and the mistakes I’m still making.

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