Chalkboard

Chalkboard Fantasy is a mid-sized pick'em app operated by Chalkboard Inc. (a Tennessee-based startup that has raised modest seed funding since 2019). It positions itself between the smaller niche apps and the PrizePicks/Underdog tier, with a cleaner interface than many competitors and a 4.6-star App Store rating across more than 17,000 reviews. Chalkboard's hook is a heavier emphasis on NFL pick'em pools alongside standard player-prop pick'ems.

Overview

The core product is over/under player prop pick'ems (2–8 legs), with a secondary NFL Pick'Em pool format where users pick weekly game winners. Sports covered are NFL, NBA, MLB, NHL, college football, college basketball, UFC, PGA and soccer. Chalkboard is live in roughly 31 states including AK, AR, CA, D.C., DE, FL, GA, IL, KS, KY, MA, ME, MN, MO, NC, ND, NE, NH, NM, OK, OR, PA, RI, SC, SD, TX, UT, VA, VT, WI and WY.

Welcome Offer

The standard offer is a $100 deposit match plus a $10 free entry on signup. Affiliate codes occasionally push the match higher. A "free first square" promo runs during major NFL weeks.

Product Depth

Standard player-vs-house pick'em math: 2-pick pays ~3x, 3-pick ~5x, 4-pick ~10x, 5-pick ~20x, 6-pick ~35x. Chalkboard's NFL Pick'Em pools are the differentiator — a weekly square-pool format that sits closer to Splash Sports' contest structure than PrizePicks. The "shield" insurance feature (refund if one pick loses on 4+ leg lineups) was removed in mid-2025 after a product review, a change that drew user complaints in App Store reviews but simplified the payout ladder.

Banking

Deposits via Visa, Mastercard, PayPal, Apple Pay. Withdrawals via PayPal (24–48 hours typical) or ACH (2–4 business days). User reviews flag occasional withdrawal delays during peak weeks but no systemic payout failures of the ThriveFantasy variety.

Ongoing Promos

• Weekly NFL free squares promo
• $100 deposit match (rotating code)
• Refer-a-friend bonus
• Boosted player cards on select slates

Regulatory Reality

Chalkboard has not been individually targeted by state cease-and-desist letters the way PrizePicks, Underdog and Betr have, which reflects its smaller footprint rather than any legal immunity. The same state-level pick'em legality questions apply: the product is unavailable in New York (2024 DFS rules), Washington, Idaho, Nevada, Montana, Arizona, Iowa, Hawaii, Connecticut, Louisiana, Mississippi, Alabama and several other sports-betting-legal states. California operation continues despite the state Attorney General's 2023 opinion that player-versus-house pick'em contests constitute unlicensed sports betting. Users should assume any state could flip.

User Experience

Chalkboard's App Store rating (4.6 stars, 17,000+ reviews) is genuinely strong for the category. The app is fast, the prop layout is clean, and the NFL pool format is well-integrated. Customer support responds via in-app chat during business hours — better than email-only competitors but worse than the 24/7 live chat at larger operators.

The Bottom Line

Chalkboard is a credible alternative to the big three pick'em apps, particularly for NFL-focused players who want both traditional player-prop lineups and weekly pool formats in one place. The product is not as deep on NBA or MLB props as PrizePicks, but the interface is clean, the company is responsive, and the welcome offer is competitive. A reasonable spot in a 3-to-5-app pick'em stack.