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Startup Founder Advice from the Midwest

Startup advice and lessons from Midwest founders and investors — cap tables, fundraising strategy, brand building, leadership challenges, and ecosystem navigation.

Startup Founder Advice from the Midwest

How Much Should You Raise? Start With the Milestone, Not the Number

How Much Should You Raise? Start With Milestones, Not the Number

October 9, 2026

START UP Season 14 on LinkedIn is focused on Ohio & Illinois

START UP Season 14 highlights Midwest entrepreneurs in Ohio and Illinois

October 3, 2026

The Craft of Passing on a Deal Why Investors say No and how they should do it

The Craft of the Pass: Why Investors Say No, and How to Do It Well

September 18, 2026

Founder Interview: Ryan Stevens of Digital Reference - From startup COO to Founder

Founder Interview: Ryan Stevens of Digital Reference - From startup COO to Founder

September 11, 2026

(Almost) Nobody Is Going to Tell You No: How to Translate a VC Pass

(Almost) Nobody Is Going to Tell You No: How to Translate a VC Pass

September 9, 2026

Building the plane while it is taking off

Before You Fundraise, Make Sure Your Company Is Real

September 4, 2026

StartMidwest Founder Story on Tim Huelskamp of 1440 in Chicago

Founder Stories: Tim Huelskamp of 1440 - newsletters for the insatiably curious

August 24, 2026

A Rocket for the Inc 5000 fastest growing companies

26 Midwest Companies in Top 250 of the Inc. 5000 Fastest Growing 2026

August 18, 2026

How Midwest builders manage pressure by Aria Spears of Michigan Founders Fund

The Weight Founders Carry: How Midwest Builders Manage Pressure

August 14, 2026

Hands fighting over a Teddy Bear cofounders relationships before they start

Playing Nice Isn't a Plan: What to Ask Your Co-Founder Before You Commit.

The Secret Founder: Belief isn't the bottleneck, execution is.

The Secret Founder: Belief isn't the bottleneck, execution is.

The infrastructure advantage by Ruby Miller build the shovel not just the goldmine

The infrastructure advantage: build the shovel, not just the goldmine

UnDemo Day 2026: Applications close this week as investors - and the NVCA - come to Detroit

Derrick Maultsby of FBT Gibbons on stage at Black Tech Week 2026 in Cincinnati.

A road trip to Cincinnati for Black Tech Week 2026.

StartMidwest what you should pay attention to at TechChicago Week from four local experts

TechChicago Week: Your Guide from those in the know.

StartMidwest - Aria Spears Experiments and lessons from small town ecosystems

Experiments and lessons learned from small town ecosystems

Quarterbacking venture due diligence, from a Detroit investor at Straylight Capital

Life as a Quarterback: Due Diligence from an investor’s perspective

The Secret VC on why almost nobody leads a startup funding round in the Midwest

The Secret VC: Everyone wants to ‘invest’, no one wants to lead.

Women Innovators Lounge at Newlab during Michigan Tech Week in Detroit

Builders below the radar: What pattern-matching might cost us

StartMidwest Cintrifuse Ilana Habib on being acquired

Acquired Isn’t Always a Happy Ending: A Conversation with Cintrifuse Capital’s Ilana Habib

Win the People, Win the Ecosystem

StartMidwest - Chicago Investors if they were star signs

Forget AUM. What's Their Star Sign?

StartMidwest Mollie Kuramoto High Alpha dangers of a broad ICP for early stage startups

Why Midwest Founders Cannot Afford Broad ICPs

StartMidwest - Backing Wonder in Growth Stage Companies by Michelle Erikson of Straylight Capital

Backing Wonder in Growth Stage Companies

The Secret Founder why does Midwest fundraising feel like applying for a job

The Secret Founder: Why does Midwest fundraising feel like applying for a job?

Front page of the 2026 State of Talent Access & Hiring Report, a Midwest startup hiring survey by StartMidwest, Digital Reference, and Purpose Jobs.

The State of Talent Access & Hiring Report 2026: What the data tells us.

StartMidwest Secret VC Funds are the entry fee of venture capital

The Secret VC: Funds are the entry fee of Venture Capital. The Real Value is Reputation.

StartMidwest - Sebastian Penix - Where is the Innovation Capital

Are We Evaluating Our Ecosystems? Or Just Counting Money?

Minnesota knows how to build: can it keep its best?

StartMidwest - High Alpha - Midwest Founders Take Longer to Raise

Midwest Founders Raise Just as Well — But It Costs More to Get There

StartMidwest - Gaming in Wisconsin - Midwest Founders Community

Virtual Reality Gaming in Southeast Wisconsin

Lay of the Land - 241 Chad Delligatti of InnoSource

StartMidwest Founder Stories: Justin Turk of ConStrat AI

Founder Stories: Justin Turk of ConStrat AI

Where Is the Innovation Capital? Midwest Investors Must Catch Up to Their Founders

February 20, 2026

The Secret VC The Secret VC: Exit Math Is Destiny - Midwest Funds and Mega Funds are playing different games

The Secret VC: Exit Math Is Destiny - Midwest Funds and Mega Funds are playing different games

February 18, 2026

StartMidwest Chris Kaufman of StockX in Detroit Founder Story

Founder Stories: Chris Kaufman of StockX

February 16, 2026

Startup Wisconsin Podcast: How UW Milwaukee Turns Research Into Startups - Jessica Silvaggi, UWM Research Foundation

Startup Wisconsin Podcast: Jessica Silvaggi of UWM Research Foundation

February 12, 2026

StartMidwest - Cincinnati doesnt need to be silicon valley

Cincinnati Doesn’t Need to Be Silicon Valley: Insights from Midwest Investing

February 13, 2026

Why More Midwest SaaS Companies Should Embrace Design Earlier

February 6, 2026

Why More Healthcare Professionals Should Be Building Startups

February 4, 2026

StartMidwest author Sebastian Penix talks about The Capital Delusion: Why Founders at Every Level Get Funding Wrong

The Capital Delusion: Why Founders at Every Level Get Funding Wrong

February 2, 2026

StartMidwest author Caroline Wolanin of Straylight Capital asks Should Founders Talk to Junior VCs? The Advice Is Right — and Also Wrong

Should Founders Talk to Junior VCs? The Advice Is Right — and Also Wrong

January 28, 2026

What you need is rhythms, not resolutions — and Michigan is the best place to create them

January 23, 2026

StartMidwest The Secret VC: Stop Asking "Who Else Is In?”

The Secret VC: Stop Asking "Who Else Is In?”

January 19, 2026

The Boomerang VC: Ilana Habib on Midwest Grit, Patient Capital, and Building Bigger in Ohio

January 15, 2026

StartMidwest The Secret Founder: Hey Midwest VCs, please stop cosplaying Silicon Valley

The Secret Founder: Hey Midwest VCs, please stop cosplaying Silicon Valley

January 12, 2026

StartMidwest Midwest Startup Founder Stories: Year in Review 2025

Midwest Startup Founder Stories: Year in Review 2025

December 23, 2025

StartMidwest How should leaders manage an accusation of inappropriate behavior?

How should leaders manage an accusation of inappropriate behavior?

December 20, 2025

StartMidwest author Mollie Kuramoto says Midwest Nice Isn’t a Bad Thing. But It’s Also Not Enough.

Midwest Nice Isn’t a Bad Thing. But It’s Also Not Enough.

December 19, 2025

StartMidwest Startup Wisconsin Podcast: Shantanu Singh of Obviate.ai

Startup Wisconsin Podcast: Shantanu Singh of Obviate.ai

December 17, 2025

StartMidwest Founder Stories: Charlie & Madeline of Intero Biosystems

Founder Stories: Charlie & Madeline of Intero Biosystems

December 15, 2025

Dual HQ, Singular Vision: Inside Kernel’s Plan to Scale a Breakout AI Company

December 10, 2025

Eastern Michigan launches Empowerment Program to help low income entrepreneurs

November 28, 2025

StartMidwest The Secret VC: Why Hustle Culture Is Toxic AF

The Secret VC: Why Hustle Culture Is Toxic AF

November 26, 2025

StartMidwest author Sebastian Penix asks WTF is an Ecosystem anyways?

WTF is an Ecosystem anyways?

November 21, 2025

StartMidwest 2025 SaaS Benchmarks: Where the Midwest Is Winning (and Where It Lags)

2025 SaaS Benchmarks: Where the Midwest Is Winning (and Where It Lags)

November 19, 2025

StartMidwest Nine years of Startup Wisconsin Week

Why We Keep Showing Up: Nine Years of Startup Wisconsin Week

November 10, 2025

StartMidwest Venture Capitalist Michelle Erikson shares What Raising a Kid & Raising a Company Have in Common

In the Trenches: What Raising a Kid & Raising a Company Have in Common

November 7, 2025

StartMidwest Our Secret VC helps explain to founders how to reframing the founder and funder relationship

The Secret VC: reframing the founder / funder relationship

October 22, 2025

StartMidwest Beyond the Parade: Hoosier Entrepreneurs Who Built at Home

Beyond the Parade: Hoosier Entrepreneurs Who Built at Home

October 17, 2025

StartMidwest Founder Stories: Ben Kvalo of Midwest Games

Founder Stories: Ben Kvalo of Midwest Games

October 13, 2025

Perseverance, Potlucks, and Potholes: Surviving Change as a Midwesterner

October 3, 2025

StartMidwest Midwest House talks to Pete Martin of MSU Research Foundation aabout the 1 million dollar PitchMI comopetition

Pete Martin of MSU Research Foundation at PitchMI 2025

October 1, 2025

StartMidwest Founder Stories: Laura Markewicz of Lotza

Founder Stories: Laura Markewicz of Lotza

September 29, 2025

StartMidwest Secret VC shares the red flags VCs look for when evaluating startups

The Secret VC: startup red flags investors don’t tell you.

September 22, 2025

Indiana: How Do States Keep Their Talent?

September 5, 2025

In Ohio, Founders Win When Community Comes First

September 3, 2025

StartMidwest Midwest House talks to Hilary Doe Chief Growth Officer for the State of Michigan

Midwest House Stories - Hilary Doe, Chief Growth Officer for the State of Michigan

StartMidwest - Will it play in Peoria

In The Middle of Everything: "Will it play in Peoria?”

StartMidwest - VC Advice whether to raise funds or not - Allie Singer

A Midwest VC’s Guide: To raise or not, tis the question

a-midwest-vcs-guide-to-raise-or-not-tis-the-question

StartMidwest The Cap Table for Founders Guide to Equity Control and Capital

The Cap Table for Founders: Guide to Equity, Control & Capital

the-cap-table-for-founders-guide-to-equity-control-capital

December 22, 2025